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Greenport West Rentals

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  • 🌟 Walk to the village ❤ of Greenport
    Click For Pricing

    VRBO

    🌟 Walk to the village ❤ of Greenport

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Stay in our Cozy Greenport home, in one of the most central and convenient locations in Greenport Village! *Amazing Wint ...

    Click For Pricing

    VRBO

    Details
  • Newly built ranch, beautifully landscaped with pool, large yard, patio,...
    From $458 per night (USD)

    Expedia

    Newly built ranch, beautifully landscaped with pool, large yard, patio,...

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Greenport Getaway Newly built ranch, beautifully landscaped with pool, large yard, patio, fire pit, ample seating, minu ...

    From $458 per night (USD)

    Expedia

    Details
  • Cleves Point Estates Home, Private sandy beach
    From $416 per night (USD)

    VRBO

    Cleves Point Estates Home, Private sandy beach

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    This beautiful house is located in a private beach community. An 8 minute walk brings you to a private beach with view ...

    From $416 per night (USD)

    VRBO

    Details
  • Beautiful, newly-remodeled home w\/ a gas fireplace, patio, & firepit - dogs OK
    From $524 per night (USD)

    Expedia

    Beautiful, newly-remodeled home w\/ a gas fireplace, patio, & firepit - dogs OK

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Greenport Village Vacationer's Delight Our calendar is updated in real-time & our nightly rates are accurately displaye ...

    From $524 per night (USD)

    Expedia

    Details
  • Gorgeous Vintage Yacht in Wine Country NY
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    VRBO

    Gorgeous Vintage Yacht in Wine Country NY

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    KINGFISHER is a stunning, 50 foot fully restored vintage motor yacht that offers timeless yachting experiences in Hampto ...

    Click For Pricing

    VRBO

    Details
  • SUMMER RETREAT: Pool + Beach + Dock overlooking the Peconic Bay in Greenport!
    From $531 per night (USD)

    Expedia

    SUMMER RETREAT: Pool + Beach + Dock overlooking the Peconic Bay in Greenport!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Welcome to Gull Harbor! The house size is deceiving. It is great for multiple families as part of it is a guest en suit ...

    From $531 per night (USD)

    Expedia

    Details
  • Beautiful home minutes away from village, restaurants, beach, and wineries!
    From $552 per night (USD)

    VRBO

    Beautiful home minutes away from village, restaurants, beach, and wineries!

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    6

    Come to our beautiful village of Greenport! Open concept home with pool. Three bedrooms four baths and large basement, ...

    From $552 per night (USD)

    VRBO

    Details
  • Greenport 'Sunshine Home'
    From $913 per night (USD)

    Expedia

    Greenport 'Sunshine Home'

    Bedrooms:
    4
    Bathrooms:
    7
    Sleeps:
    10

    This welcoming colonial is situated on three-fourths of an acre. Family friendly, the house is perfect for your time awa ...

    From $913 per night (USD)

    Expedia

    Details
  • Greenport Log Home in the woods…near the water.          Rental registry # 0952
    From $919 per night (USD)

    VRBO

    Greenport Log Home in the woods…near the water. Rental registry # 0952

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    PLEASE READ FULL DESCRIPTION! Rental registry # 0952 Private modern 4 bedroom/2 bath cabin near the bay situated on 3.8 ...

    From $919 per night (USD)

    VRBO

    Details
  • New Four-bed Home with private Beach access for Rent
    From $744 per night (USD)

    Expedia

    New Four-bed Home with private Beach access for Rent

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Modern, brand new, house, with private beach, for rent. Experience North Fork summer living in this newly constructed ...

    From $744 per night (USD)

    Expedia

    Details
  • Spacious North Fork Home in Greenport, Heated Pool, Perfect for Families
    From $485 per night (USD)

    VRBO

    Spacious North Fork Home in Greenport, Heated Pool, Perfect for Families

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Greenport Cove Contemporary Spacious North Fork Home in Greenport, Heated Pool, Perfect for Families 4BR/3.5BA: privat ...

    From $485 per night (USD)

    VRBO

    Details
  • Greenport Village walking distance to all
    From $1013 per night (USD)

    Expedia

    Greenport Village walking distance to all

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    9

    3 bedroom 2 floor cape with large great room and enclosed patio perfect for families and small groups. Relax in the hot ...

    From $1013 per night (USD)

    Expedia

    Details
  • New Four Bedroom Greenport House Sleeps 10
    From $732 per night (USD)

    VRBO

    New Four Bedroom Greenport House Sleeps 10

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Spacious Greenport 2600 square foot Four Bedroom Cottage Beach Bungalow. Five minute waking distance to Greenport Villag ...

    From $732 per night (USD)

    VRBO

    Details
  • North Beach Fork Beach House
    From $349 per night (USD)

    VRBO

    North Beach Fork Beach House

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Enjoy our tranquil home in a private beach community.Located on a half acre of private land, this home has all the ameni ...

    From $349 per night (USD)

    VRBO

    Details
  • Walk to Beach and Greenport Village, Two King Beds
    From $615 per night (USD)

    VRBO

    Walk to Beach and Greenport Village, Two King Beds

    Bedrooms:
    1
    Bathrooms:
    4
    Sleeps:
    8

    A quiet Cape home within walking distance to all Greenport Village has to offer - dining, shopping, the beach and transp ...

    From $615 per night (USD)

    VRBO

    Details
  • Overlook a Vineyard, Walk to the Beach, and only a Short Walk to Town - 5 Star!
    From $669 per night (USD)

    VRBO

    Overlook a Vineyard, Walk to the Beach, and only a Short Walk to Town - 5 Star!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    6

    Discounts available for stays >14 days. Please inquire prior to booking for details. Completely updated, modern and li ...

    From $669 per night (USD)

    VRBO

    Details
  • Beautiful condo on the Long Island Sound in a resort
    From $299 per night (USD)

    VRBO

    Beautiful condo on the Long Island Sound in a resort

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This condo is one of the nicest decorated in Cliffside. Gorgeous shiplap walls with navy accents. It has a beautiful f ...

    From $299 per night (USD)

    VRBO

    Details
  • Greenport Waterfront Private Dock
    From $742 per night (USD)

    VRBO

    Greenport Waterfront Private Dock

    Bedrooms:
    3
    Bathrooms:
    6
    Sleeps:
    8

    GREENPORT CONKLING PT CREEKFRONT MINT 3BR COTTAGE W/PRIME VIEWS - This cottage on a half-acre lot fronts on the pristine ...

    From $742 per night (USD)

    VRBO

    Details
  • Waterfront Condo C204 At The Cliffside Resort With Amazing Water & Sunset Views
    From $424 per night (USD)

    VRBO

    Waterfront Condo C204 At The Cliffside Resort With Amazing Water & Sunset Views

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Waterfront Water's Edge luxury suite, Suite C-204 accommodates up to 6 guests (see below) with two bedrooms and two bath ...

    From $424 per night (USD)

    VRBO

    Details
  • NOFO  ESCAPE relax-swim-enjoy. Bachelorettes-Weddings-Family vacation
    From $705 per night (USD)

    VRBO

    NOFO ESCAPE relax-swim-enjoy. Bachelorettes-Weddings-Family vacation

    Bedrooms:
    6
    Bathrooms:
    6
    Sleeps:
    12

    Bachelorette, weddings and big party escape. Go fishing, boating, hiking, golfing, antique shopping etc walk to town, wa ...

    From $705 per night (USD)

    VRBO

    Details
  • Greenport renovated farmhouse
    From $713 per night (USD)

    VRBO

    Greenport renovated farmhouse

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    6

    Entirely renovated, spacious and quiet farmhouse two blocks from the marina, and a 5 minute bike ride to the beach or to ...

    From $713 per night (USD)

    VRBO

    Details
  • Newly Renovated Summer Retreat, Heated Pool, Walk to Beach, Designer Furnishings
    From $760 per night (USD)

    VRBO

    Newly Renovated Summer Retreat, Heated Pool, Walk to Beach, Designer Furnishings

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    *30 day minimum rental* Newly renovated modern farmhouse on a spacious property with a large heated saltwater pool and p ...

    From $760 per night (USD)

    VRBO

    Details
  • Peaceful Retreat with 100 ft private deep water dock
    From $511 per night (USD)

    VRBO

    Peaceful Retreat with 100 ft private deep water dock

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Comfortable waterfront home with private dock and large yard. Three bedrooms and two full baths. The house has Cable TV, ...

    From $511 per night (USD)

    VRBO

    Details
  • Relax in this light-filled home, steps from the beach and a short walk to town!
    From $424 per night (USD)

    VRBO

    Relax in this light-filled home, steps from the beach and a short walk to town!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    The perfect getaway. Within walking distance to beach, town, Jitney, LIRR and ferries to the South Fork. This quiet and ...

    From $424 per night (USD)

    VRBO

    Details
  • Antique house, Private & Peaceful Oasis
    From $775 per night (USD)

    VRBO

    Antique house, Private & Peaceful Oasis

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Newly restored antique home, 3 bedrooms, 1.5 baths with outdoor shower surrounded by manicured lawn & bucolic grounds. ...

    From $775 per night (USD)

    VRBO

    Details
  • Beautifully decorated water view resort condo
    From $434 per night (USD)

    VRBO

    Beautifully decorated water view resort condo

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Cliffside Resort is located on a bluff overlooking the Long Island sound with beautiful water vistas. The resort has an ...

    From $434 per night (USD)

    VRBO

    Details
  • Greenport,  North Fork, Beach, Designer Chic, Vineyard Views, Hamptons luxury
    From $531 per night (USD)

    VRBO

    Greenport, North Fork, Beach, Designer Chic, Vineyard Views, Hamptons luxury

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    9

    Charming, private, sun filled 3 bedroom Designer country home with fireplace, spacious living area including den/library ...

    From $531 per night (USD)

    VRBO

    Details
  • Cottage on Beach front Estate .Walk to Village
    From $342 per night (USD)

    VRBO

    Cottage on Beach front Estate .Walk to Village

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    4

    Charming 2-bedroom cottage located on a family-owned waterfront estate that was converted from a circa 1920s chicken coo ...

    From $342 per night (USD)

    VRBO

    Details
  • Seaside seclusion, salt water sanctuary!
    From $400 per night (USD)

    VRBO

    Seaside seclusion, salt water sanctuary!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Greenport is a charming seaside town with historic architecture with awesome restaurants and plenty to see and do! Trav ...

    From $400 per night (USD)

    VRBO

    Details
  • Dream Beach House on the North Fork: Waterfront, Private Beach + Stunning Views
    From $1345 per night (USD)

    VRBO

    Dream Beach House on the North Fork: Waterfront, Private Beach + Stunning Views

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    One of the nicest spots on the North Fork (that's a quote from a knowledgeable local!), beautifully designer-renovated b ...

    From $1345 per night (USD)

    VRBO

    Details
  • NEW VICTORIAN GEM IN GREENPORT
    From $715 per night (USD)

    VRBO

    NEW VICTORIAN GEM IN GREENPORT

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    12

    Newly renovated Victorian house in Greenport. 5 queen bedrooms with private full baths, spacious, super clean and meticu ...

    From $715 per night (USD)

    VRBO

    Details
  • POOL + Private Beach near Greenport Village!
    From $410 per night (USD)

    VRBO

    POOL + Private Beach near Greenport Village!

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    11

    Make yourself at home in this 4 bedroom / 3 full bathroom modern ranch featuring: * chef's eat-in kitchen w/ 2 ovens, lu ...

    From $410 per night (USD)

    VRBO

    Details
  • Charming Northfork Getaway
    From $317 per night (USD)

    VRBO

    Charming Northfork Getaway

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Newly renovated and charming home in the NorthFork, a short walk to the village of Greenport, vineyards, and the breatht ...

    From $317 per night (USD)

    VRBO

    Details
  • 'The Gate House' on Beach front Estate Walk to Village
    From $351 per night (USD)

    VRBO

    'The Gate House' on Beach front Estate Walk to Village

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    4

    Located on a family-owned waterfront estate, The Gate House, a cozy 2-story, 2-bedroom cottage, is only steps away from ...

    From $351 per night (USD)

    VRBO

    Details
  • Beautiful Renovated Beachfront Home
    From $692 per night (USD)

    VRBO

    Beautiful Renovated Beachfront Home

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    High on a bluff overlooking the Sound, this amazing Sound front home has been completely renovated with a chef's gourmet ...

    From $692 per night (USD)

    VRBO

    Details
  • Beach and waterfront Estate - One of a Kind Vacation House
    From $1184 per night (USD)

    VRBO

    Beach and waterfront Estate - One of a Kind Vacation House

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    10

    Same location I have two 2 cottages that sleep 4 each . See VRBO search bar [Where To] with the Listing ID 173361 and th ...

    From $1184 per night (USD)

    VRBO

    Details
  • Your Summer Escape
    Click For Pricing

    VRBO

    Your Summer Escape

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    9

    This is a fully equipped home with an open floor plan kitchen and living room, a dining room, screened-in sunroom, a la ...

    Click For Pricing

    VRBO

    Details
  • One bedroom Pied a Terre -  a lovely new and clean Greenport  place
    From $367 per night (USD)

    VRBO

    One bedroom Pied a Terre - a lovely new and clean Greenport place

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Rental Permit 1063 Live the perfect life with a new Pied a Terre on the North Fork in Greenport. This lovely one bedr ...

    From $367 per night (USD)

    VRBO

    Details
  • Peaceful. Unique. Modern
    From $1695 per night (USD)

    VRBO

    Peaceful. Unique. Modern

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    This brand new modern home offers everything you could ask for from a summer retreat in Greenport. Two story height grea ...

    From $1695 per night (USD)

    VRBO

    Details
  • Pristine waterfront home with direct access to private bay and dock,...
    From $523 per night (USD)

    VRBO

    Pristine waterfront home with direct access to private bay and dock,...

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Please note that a reservation for this property needs to be approved before it is confirmed. Snug Harbor Stylish Pris ...

    From $523 per night (USD)

    VRBO

    Details
  • Beach House near Greenport Village
    From $830 per night (USD)

    VRBO

    Beach House near Greenport Village

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    8

    3 bedroom with deeded beach rights and partial water view. 5 minute walk to the beach and short drive to the heart of th ...

    From $830 per night (USD)

    VRBO

    Details
  • Paradise home in Greenport beach town
    Click For Pricing

    Expedia

    Paradise home in Greenport beach town

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    A traditional cedar shingle beach house, with comfortable contemporary interiors. Nestled on 1 acre of carefully landsca ...

    Click For Pricing

    Expedia

    Details
  • Updated and dog-friendly, close to seasonal activities with yard, & washer\/dryer
    From $447 per night (USD)

    VRBO

    Updated and dog-friendly, close to seasonal activities with yard, & washer\/dryer

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Modern on 9th Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...

    From $447 per night (USD)

    VRBO

    Details
  • 4BR Cape Home w Lg Screened Porch.  1m walk\/drive Greenport Shops + Dining.
    From $461 per night (USD)

    VRBO

    4BR Cape Home w Lg Screened Porch. 1m walk\/drive Greenport Shops + Dining.

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Renovated cape-style home with central AC - Living room w55" Smart TV + sound system - Sunny, large den with w65" Smart ...

    From $461 per night (USD)

    VRBO

    Details
  • Charming '30s cottage on water overlooking Shelter Island—5 mins from Greenport.
    Click For Pricing

    VRBO

    Charming '30s cottage on water overlooking Shelter Island—5 mins from Greenport.

    Bedrooms:
    1
    Bathrooms:
    4
    Sleeps:
    6

    Breezy Shores is like no other place on the North Fork. Our 1930s cottage is set on 80 acres of private, waterfront prop ...

    Click For Pricing

    VRBO

    Details
  • Peaceful, clean cottage, 10 min walk to town. Monthly rates. Fenced backyard
    From $258 per night (USD)

    VRBO

    Peaceful, clean cottage, 10 min walk to town. Monthly rates. Fenced backyard

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    We welcome you to our cottage away from it all but still close to all activities that make the North Fork a magical plac ...

    From $258 per night (USD)

    VRBO

    Details
  • Cozy Greenport village cottage
    From $924 per night (USD)

    VRBO

    Cozy Greenport village cottage

    Bedrooms:
    5
    Bathrooms:
    4
    Sleeps:
    8

    Family friendly cottage, nestled in a quiet street in Greenport village. The private property has fully fenced backyard, ...

    From $924 per night (USD)

    VRBO

    Details
  • Greenport Waterfront Cottage w\/Private Beach
    From $500 per night (USD)

    VRBO

    Greenport Waterfront Cottage w\/Private Beach

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Located in the historic and centuries-old town of Greenport Village with its quiet streets, serious dining options and ...

    From $500 per night (USD)

    VRBO

    Details
  • Cozy Greenport Cottage | House in Greenport with a private pool & sauna
    From $364 per night (USD)

    VRBO

    Cozy Greenport Cottage | House in Greenport with a private pool & sauna

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    10

    Cozy Greenport Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...

    From $364 per night (USD)

    VRBO

    Details
  • Greenport Villa with a Pool
    From $1607 per night (USD)

    VRBO

    Greenport Villa with a Pool

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    10

    Bring the whole family to this great place with lots of room for indoor and outdoor activities! Enjoy an entire Greenp ...

    From $1607 per night (USD)

    VRBO

    Details
  • The Saltbox Greenport-19th Century meets 21st Century
    From $703 per night (USD)

    VRBO

    The Saltbox Greenport-19th Century meets 21st Century

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    This unique home has a style all its own. Stylish and chic, an impeccably restored historic Salt Box. It boasts an updat ...

    From $703 per night (USD)

    VRBO

    Details
  • Luxurious living in Greenport's private Rock Cove Estates on the sound
    From $1280 per night (USD)

    VRBO

    Luxurious living in Greenport's private Rock Cove Estates on the sound

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    12

    2024 Rates: MD-June $28k, June $25k July $35k , Weekly rental $8,500/ week 2 week minimum. Luxurious living in Greenpor ...

    From $1280 per night (USD)

    VRBO

    Details
  • Exquisite dog-friendly home with large yard, furnished porch, & firepit
    From $380 per night (USD)

    VRBO

    Exquisite dog-friendly home with large yard, furnished porch, & firepit

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Serene Bay Breezes - Private Bay Beach Community Our calendar is updated in real-time & our nightly rates are accuratel ...

    From $380 per night (USD)

    VRBO

    Details
  • Greenport Getaway w\/Pool & Fire Pit
    From $645 per night (USD)

    VRBO

    Greenport Getaway w\/Pool & Fire Pit

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Welcome to this stunning & newly renovated Greenport home. This magnificent home seamlessly blends comfort, style and lu ...

    From $645 per night (USD)

    VRBO

    Details
  • Waterfront Beach House Gem with Bay Views Steps to Pipes Cove!
    From $857 per night (USD)

    VRBO

    Waterfront Beach House Gem with Bay Views Steps to Pipes Cove!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Our Greenport beach house is steps from Pipes Cove Beach with beach access, water views from the house, a big yard, and ...

    From $857 per night (USD)

    VRBO

    Details
  • Park-like setting, private lane, walk to beach, close to town. Boats welcome.
    From $352 per night (USD)

    VRBO

    Park-like setting, private lane, walk to beach, close to town. Boats welcome.

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    5

    Enjoy this spacious one level home with all the amenities located on a quiet private lane, yet so close to the beach! S ...

    From $352 per night (USD)

    VRBO

    Details
  • Perfect Greenport Retreat
    Click For Pricing

    VRBO

    Perfect Greenport Retreat

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Walk and/or bike everywhere you want from this gem. Rarely rented out, my personal summer rental. Be one of the first t ...

    Click For Pricing

    VRBO

    Details
  • Waterfront + Complete Gym + Hot tub
    Click For Pricing

    Expedia

    Waterfront + Complete Gym + Hot tub

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Renovated, waterfront property within close proximity to everything. Outstanding high speed internet, a perfect setup fo ...

    Click For Pricing

    Expedia

    Details
  • Renovated 4-Bedroom House with Heated Pool & Private Beach Access
    From $309 per night (USD)

    VRBO

    Renovated 4-Bedroom House with Heated Pool & Private Beach Access

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Incredible beach house just minutes from Greenport! This freshly renovated home is a dream family vacation spot. It's ...

    From $309 per night (USD)

    VRBO

    Details
  • Cozy stylish home walking distance from private beach.
    From $701 per night (USD)

    VRBO

    Cozy stylish home walking distance from private beach.

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    This home is in a quiet community walking distance from a private beach. Driveway parking on premises in a gated drivewa ...

    From $701 per night (USD)

    VRBO

    Details
  • Bright and Modern North Fork Living
    From $482 per night (USD)

    VRBO

    Bright and Modern North Fork Living

    Bedrooms:
    1
    Bathrooms:
    4
    Sleeps:
    5

    Enjoy all the best the North Fork has to offer. Newly renovated Cape Cod style home walkable to beaches, marinas, resta ...

    From $482 per night (USD)

    VRBO

    Details
  • Sensational, newly remodeled waterfront Greenport condo
    From $222 per night (USD)

    VRBO

    Sensational, newly remodeled waterfront Greenport condo

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    A beautiful waterfront condo just a short walk from historic Greenport village, this newly remodeled unit provides stunn ...

    From $222 per night (USD)

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    Details
  • Quiet street one block to shops, restaurants & waterfront. Barn with TV & WIFI
    From $569 per night (USD)

    VRBO

    Quiet street one block to shops, restaurants & waterfront. Barn with TV & WIFI

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Three bedrooms, 2 bathrooms completely renovated home. Sleeps 6. One full bath, one half bath. Outdoor shower. Fully ren ...

    From $569 per night (USD)

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    Details
  • TRANQUIL RESORT STYLE RETREAT WITH LUXURY GUNITE POOL 2 MIN FROM SANDY BEACHES
    From $1050 per night (USD)

    Expedia

    TRANQUIL RESORT STYLE RETREAT WITH LUXURY GUNITE POOL 2 MIN FROM SANDY BEACHES

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    This newly renovated sun-drenched Shelter Island retreat with an exquisite 21'x42' Gunite, wifi-enabled luxury heated po ...

    From $1050 per night (USD)

    Expedia

    Details
  • Enchanting home with beautiful bay views in the heart of Greenport Village
    From $841 per night (USD)

    VRBO

    Enchanting home with beautiful bay views in the heart of Greenport Village

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Enchanted home with beautiful bay views. This house has it all. Modern updates with old-world charm. Gorgeous chefs ki ...

    From $841 per night (USD)

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    Details
  • Northfork Townhouse- walk to all\/ newly renovated
    From $412 per night (USD)

    Expedia

    Northfork Townhouse- walk to all\/ newly renovated

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Fully Renovated Townhouse walking distance to town, beaches, parks, brewery and short bike to wineries. Brand new Kitche ...

    From $412 per night (USD)

    Expedia

    Details
  • Relax and Enjoy!
    From $2196 per night (USD)

    VRBO

    Relax and Enjoy!

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    10

    Stretch out and relax in this well-designed home high on a hill with truly spectacular water views from every room. Enjo ...

    From $2196 per night (USD)

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    Details
  • Spacious Waterfront Home with Outstanding Waterviews!
    From $614 per night (USD)

    Expedia

    Spacious Waterfront Home with Outstanding Waterviews!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    9

    Fabulous four bedroom waterfront home located on a private road on Hashamomuck Pond. Sit back, relax in the backyard an ...

    From $614 per night (USD)

    Expedia

    Details
  • Beach Front House with Amazing Views on Private Beach
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    VRBO

    Beach Front House with Amazing Views on Private Beach

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Freshly renovated beautiful beach front house on private beach. This quaint 2 bedrooms, 1 1/2 bathroom house has centra ...

    Click For Pricing

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    Details
  • Shore House - A Luxury Beach Retreat
    From $2574 per night (USD)

    Expedia

    Shore House - A Luxury Beach Retreat

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    This extraordinary modern home offers an abundance of amenities with easy access to the white sands of Sunset Beach. Per ...

    From $2574 per night (USD)

    Expedia

    Details
  • Greenport Village Getaway
    From $802 per night (USD)

    VRBO

    Greenport Village Getaway

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Welcome to the Greenport Getaway! Located in the center of the Greenport Village, this spacious residential home boasts ...

    From $802 per night (USD)

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    Details
  • Elegant Victorian in the Heart of Greenport
    From $1128 per night (USD)

    Expedia

    Elegant Victorian in the Heart of Greenport

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    13

    Winter Harbor House is a stylish Victorian walking distance from the best restaurants, bars and beaches in Greenport Vil ...

    From $1128 per night (USD)

    Expedia

    Details
  • Renovated and Spacious Summer Home with Water View on Picturesque Island.
    From $775 per night (USD)

    VRBO

    Renovated and Spacious Summer Home with Water View on Picturesque Island.

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Steps from the beach, this beach house is the perfect destination to enjoy beautiful Shelter Island. Recently renovated ...

    From $775 per night (USD)

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    Details
  • Waterfront Bungalow w\/ Private Beach on Peconic Bay
    From $199 per night (USD)

    VRBO

    Waterfront Bungalow w\/ Private Beach on Peconic Bay

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    7

    Relax on your private Beach, hit the Vineyard Trail, stroll around Downtown Greenport or ferry to Shelter Island, friend ...

    From $199 per night (USD)

    VRBO

    Details
  • Quaint DT Greenport Apt - 2 Mi to Shelter Island!
    From $275 per night (USD)

    VRBO

    Quaint DT Greenport Apt - 2 Mi to Shelter Island!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Surround yourself with seaside charm at this Greenport vacation rental. Perfect for couples and solo travelers, this 1-b ...

    From $275 per night (USD)

    VRBO

    Details
  • Bright Apartment - 1\/2 Mi to Greenport Harbor!
    From $348 per night (USD)

    Expedia

    Bright Apartment - 1\/2 Mi to Greenport Harbor!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Combine peace and quiet with bustling downtown action when you book this charming Greenport vacation rental! The 1-bedro ...

    From $348 per night (USD)

    Expedia

    Details
  • Lavender Fields Retreat: Nearby the Beach & Farms
    From $464 per night (USD)

    VRBO

    Lavender Fields Retreat: Nearby the Beach & Farms

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Situated on the North Fork of Long Island in the hamlet of East Marion, New York. This charming Lavender Fields Retreat ...

    From $464 per night (USD)

    VRBO

    Details
  • Brand new 2 bedroom, Greenport Village, walk to town Marina Views!!
    From $366 per night (USD)

    Expedia

    Brand new 2 bedroom, Greenport Village, walk to town Marina Views!!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Luxury 2 bedroom, first floor apartment located across the street from Townsend Manor Marina in the heart of Greenport V ...

    From $366 per night (USD)

    Expedia

    Details
  • 1820 Whaling Captain's Home
    From $496 per night (USD)

    VRBO

    1820 Whaling Captain's Home

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

    Set in the historic section of Greenport village, the Captain’s House, built in 1820, is an elegant and charming 3 bedro ...

    From $496 per night (USD)

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    Details
  • American Beech in Greenport - Two-Bedroom Apartment 8
    From $351 per night (USD)

    Expedia

    American Beech in Greenport - Two-Bedroom Apartment 8

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    The 19th-century historic and centrally located Stirling Square in Greenport Village has been reimagined into the modern ...

    From $351 per night (USD)

    Expedia

    Details
  • American Beech in Greenport  - Deluxe King Suite 11
    From $260 per night (USD)

    VRBO

    American Beech in Greenport - Deluxe King Suite 11

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    The 19th-century historic and centrally located Stirling Square in Greenport Village has been reimagined into the modern ...

    From $260 per night (USD)

    VRBO

    Details
  • American Beech - Deluxe King 5
    From $234 per night (USD)

    Expedia

    American Beech - Deluxe King 5

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    The 19th-century historic and centrally located Stirling Square in Greenport Village has been reimagined into the modern ...

    From $234 per night (USD)

    Expedia

    Details
  • American Beech in Greenport - Deluxe King Suite 12
    From $260 per night (USD)

    VRBO

    American Beech in Greenport - Deluxe King Suite 12

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    The 19th-century historic and centrally located Stirling Square in Greenport Village has been reimagined into the modern ...

    From $260 per night (USD)

    VRBO

    Details
  • American Beech in Greenport - Deluxe King 4
    From $260 per night (USD)

    Expedia

    American Beech in Greenport - Deluxe King 4

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    The 19th-century historic and centrally located Stirling Square in Greenport Village has been reimagined into the modern ...

    From $260 per night (USD)

    Expedia

    Details
  • American Beech in Greenport NY - King Suite 1
    From $234 per night (USD)

    VRBO

    American Beech in Greenport NY - King Suite 1

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    The 19th-century historic and centrally located Stirling Square in Greenport Village has been reimagined into the modern ...

    From $234 per night (USD)

    VRBO

    Details
  • American Beech - Luxury 2 Bedroom Apartment 10
    From $351 per night (USD)

    Expedia

    American Beech - Luxury 2 Bedroom Apartment 10

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    The 19th-century historic and centrally located Stirling Square in Greenport Village has been reimagined into the modern ...

    From $351 per night (USD)

    Expedia

    Details
  • American Beech - Deluxe King Suite 14
    From $298 per night (USD)

    VRBO

    American Beech - Deluxe King Suite 14

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    The 19th-century historic and centrally located Stirling Square in Greenport Village has been reimagined into the modern ...

    From $298 per night (USD)

    VRBO

    Details
  • American Beech - King Suite 2
    From $234 per night (USD)

    Expedia

    American Beech - King Suite 2

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    The 19th-century historic and centrally located Stirling Square in Greenport Village has been reimagined into the modern ...

    From $234 per night (USD)

    Expedia

    Details
  • American Beech in Greenport - Deluxe King 6
    From $234 per night (USD)

    VRBO

    American Beech in Greenport - Deluxe King 6

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    The 19th-century historic and centrally located Stirling Square in Greenport Village has been reimagined into the modern ...

    From $234 per night (USD)

    VRBO

    Details
  • American Beech in Greenport - King Suite 3
    From $274 per night (USD)

    Expedia

    American Beech in Greenport - King Suite 3

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    The 19th-century historic and centrally located Stirling Square in Greenport Village has been reimagined into the modern ...

    From $274 per night (USD)

    Expedia

    Details
  • Greenport Walk to beach & vineyard from this brand new home
    From $688 per night (USD)

    VRBO

    Greenport Walk to beach & vineyard from this brand new home

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Take it easy at this brand new unique retreat. Walking to distance to the beach and winery. Less than a 2 minute drive ...

    From $688 per night (USD)

    VRBO

    Details
  • Charming Historic Farmhouse in Greenport Village
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    Expedia

    Charming Historic Farmhouse in Greenport Village

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Beautiful Greenport Village Farmhouse situated on .37 Acres. Built in 1822 and restored with modern amenities. This is t ...

    Click For Pricing

    Expedia

    Details
  • Newly renovated ranch with large pool in a quiet neighborhood, off main road
    From $461 per night (USD)

    VRBO

    Newly renovated ranch with large pool in a quiet neighborhood, off main road

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Private home in quiet neighborhood Make yourself at home in this 3 bedroom, 2 full bathroom modern ranch featuring: ...

    From $461 per night (USD)

    VRBO

    Details
  • Updated Historic shingle-style 1902 4-bedroom Beach House on Southold Bay!
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    Expedia

    Updated Historic shingle-style 1902 4-bedroom Beach House on Southold Bay!

    Bedrooms:
    5
    Bathrooms:
    4
    Sleeps:
    8

    You are invited to have a wonderful time in this Southold, Long Island beach house. You will have a fabulous time of sun ...

    Click For Pricing

    Expedia

    Details
  • Tranquil 3BR Shelter Island Beach House with Private Beach Access
    From $1007 per night (USD)

    VRBO

    Tranquil 3BR Shelter Island Beach House with Private Beach Access

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    10

    Tranquil getaway in Shelter Island with private beach access. Modern, bright home newly decorated by top design firm is ...

    From $1007 per night (USD)

    VRBO

    Details
  • Stylish beach getaway: pool in prime location
    From $857 per night (USD)

    VRBO

    Stylish beach getaway: pool in prime location

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to our beautifully renovated, designer-decorated home in the heart of Southold, NY! Perfectly located within wal ...

    From $857 per night (USD)

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    Details
  • Waterfront Southold Retreat < 3 Mi to Wineries!
    From $272 per night (USD)

    VRBO

    Waterfront Southold Retreat < 3 Mi to Wineries!

    Bedrooms:
    3
    Bathrooms:
    6
    Sleeps:
    8

    Escape to 'Kayak Point' and experience the beauty of Long Island's North Fork! This 4-bedroom, 2.5-bath home in Southold ...

    From $272 per night (USD)

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    Details
  • Thanksgiving -  Group Holidays rental with staff!
    From $1892 per night (USD)

    Expedia

    Thanksgiving - Group Holidays rental with staff!

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    10

    Luxury, warm, contemporary art. En suite guest rooms. Walk to Sunset Beach and TOP restaurant: Leon 1909. Cotton lin ...

    From $1892 per night (USD)

    Expedia

    Details
  • Historic Waterfront Home. Steps to North Ferry & Beach Club. Easy access to LIRR
    From $862 per night (USD)

    VRBO

    Historic Waterfront Home. Steps to North Ferry & Beach Club. Easy access to LIRR

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    6

    Our historic 5-bedroom Victorian home on Shelter Island Sound in the Heights has been in our family for 100 years. Buil ...

    From $862 per night (USD)

    VRBO

    Details
  • Historic 1830s Greenport Home
    From $206 per night (USD)

    VRBO

    Historic 1830s Greenport Home

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    6

    2024 AVAILABILITY! Looking to escape the city for a couple of weeks or even a month? The house is well set up for wor ...

    From $206 per night (USD)

    VRBO

    Details