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  • Bellport\/E. Patchogue, 4 Bed, 3 Bath, Waterfront.
    From $1095 per night (USD)

    VRBO

    Bellport\/E. Patchogue, 4 Bed, 3 Bath, Waterfront.

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    6

    Stunning beach house. Quiet, wooded location at the end of dead end street on the bay. Very quiet. Year round views of G ...

    From $1095 per night (USD)

    VRBO

    Details
  • Paradise so close to NYC
    Click For Pricing

    Expedia

    Paradise so close to NYC

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    This home is a beautifully kept 2-bedroom house, perfect for family or friends. 1 block from the beach and 1 block fro ...

    Click For Pricing

    Expedia

    Details
  • Waterfront Bungalow w\/ Private Beach on Peconic Bay
    From $271 per night (USD)

    VRBO

    Waterfront Bungalow w\/ Private Beach on Peconic Bay

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    7

    Enjoy a variety of activities when staying at this charming bungalow with a private beach on the Peconic Bay. Enjoy the ...

    From $271 per night (USD)

    VRBO

    Details
  • Charming Hampton house
    From $555 per night (USD)

    Expedia

    Charming Hampton house

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Chic, newly done 3 bedroom 2 baths home with open-plan living, located in the Town of Southampton. Right between the H ...

    From $555 per night (USD)

    Expedia

    Details
  • Contemporary Beach Cottage - Walk to Bay, Minutes from Ocean
    Click For Pricing

    VRBO

    Contemporary Beach Cottage - Walk to Bay, Minutes from Ocean

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    This contemporary cottage is located just steps from the Peconic Bay, and minutes from beautiful Ponquogue Ocean Beach o ...

    Click For Pricing

    VRBO

    Details
  • The Lady's Slipper in East Hampton
    From $2005 per night (USD)

    Expedia

    The Lady's Slipper in East Hampton

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    6

    Nestled in the white pines of East Hampton this one of a kind gated property is a quiet oasis conveniently located betwe ...

    From $2005 per night (USD)

    Expedia

    Details
  • Bayfront Vacation Home in Southold, 5 Bedrooms
    From $738 per night (USD)

    VRBO

    Bayfront Vacation Home in Southold, 5 Bedrooms

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    8

    Take in the extensive views from this lovely Goose Creek Front waterfront vacation home, with private deck and beach. To ...

    From $738 per night (USD)

    VRBO

    Details
  • Newly Renovated Montauk Condo with Ocean Views!
    From $530 per night (USD)

    Expedia

    Newly Renovated Montauk Condo with Ocean Views!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    This newly renovated, beautiful Montauk condo is a perfect space to come enjoy everything that the area has to offer. Th ...

    From $530 per night (USD)

    Expedia

    Details
  • Experience the North Fork!
    Click For Pricing

    VRBO

    Experience the North Fork!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    This beautifully renovated farmhouse is centrally located next to multiple award-winning wineries which is why we named ...

    Click For Pricing

    VRBO

    Details
  • East Hampton Luxury: Heated Pool, Hot Tub & Expansive Yard with 6 Bedrooms
    From $1927 per night (USD)

    Expedia

    East Hampton Luxury: Heated Pool, Hot Tub & Expansive Yard with 6 Bedrooms

    Bedrooms:
    4
    Bathrooms:
    6
    Sleeps:
    14

    Located down a private drive and through a stone pillared entry, this 1.4 acre oasis is within 2 miles of several white ...

    From $1927 per night (USD)

    Expedia

    Details
  • Alluring Hampton Bays Hideaway < 2 Mi to Beach!
    From $572 per night (USD)

    VRBO

    Alluring Hampton Bays Hideaway < 2 Mi to Beach!

    Bedrooms:
    2
    Bathrooms:
    6
    Sleeps:
    11

    Relax and experience fun right at your fingertips when you book this 5-bedroom, 2-bath Hampton Bays vacation rental. Upo ...

    From $572 per night (USD)

    VRBO

    Details
  • Private mediterranean waterfront estate with heated inground pool
    Click For Pricing

    Expedia

    Private mediterranean waterfront estate with heated inground pool

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    This house has 4 large bedrooms and 4 full bathrooms and sleeps 8 comfortably. It has a professional gourmet kitchen wi ...

    Click For Pricing

    Expedia

    Details
  • Luxe Waterfront East Quogue Home w\/ Beach On-Site!
    From $962 per night (USD)

    VRBO

    Luxe Waterfront East Quogue Home w\/ Beach On-Site!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Discover the breathtaking beauty of the Hamptons up close and personal when you stay at this 4-bedroom, 3-bathroom East ...

    From $962 per night (USD)

    VRBO

    Details
  • Quaint Family-sized Home w\/private beach ā€” 5 minutes from wineries!
    From $494 per night (USD)

    VRBO

    Quaint Family-sized Home w\/private beach — 5 minutes from wineries!

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    10

    This home is newly updated and on a private beach on the North Fork of Long Island, overlooking the Peconic Bay. It's pe ...

    From $494 per night (USD)

    VRBO

    Details
  • Hampton Private House near Georgica Beach
    From $1677 per night (USD)

    VRBO

    Hampton Private House near Georgica Beach

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Family 3 bedroom, 3 bathrooms house set a way back from the road, secluded by 1 acre of green land with pine trees, whit ...

    From $1677 per night (USD)

    VRBO

    Details
  • American Beech in Greenport - Two-Bedroom Apartment 8
    From $436 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 $436 per night (USD)

    Expedia

    Details
  • American Beech in Greenport  - Deluxe King Suite 11
    From $508 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 $508 per night (USD)

    VRBO

    Details
  • American Beech - Deluxe King 5
    From $296 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 $296 per night (USD)

    Expedia

    Details
  • American Beech in Greenport - Deluxe King Suite 12
    From $484 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 $484 per night (USD)

    VRBO

    Details
  • American Beech in Greenport - Deluxe King 4
    From $294 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 $294 per night (USD)

    Expedia

    Details
  • American Beech in Greenport NY - King Suite 1
    From $272 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 $272 per night (USD)

    VRBO

    Details
  • American Beech - Luxury 2 Bedroom Apartment 10
    From $755 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 $755 per night (USD)

    Expedia

    Details
  • American Beech - Deluxe King Suite 14
    From $576 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 $576 per night (USD)

    VRBO

    Details
  • American Beech - King Suite 2
    From $268 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 $268 per night (USD)

    Expedia

    Details
  • American Beech in Greenport - Deluxe King 6
    From $514 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 $514 per night (USD)

    VRBO

    Details
  • American Beech in Greenport - King Suite 3
    From $534 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 $534 per night (USD)

    Expedia

    Details
  • Sun filled 2-bedroom steps away from the beach
    From $720 per night (USD)

    VRBO

    Sun filled 2-bedroom steps away from the beach

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Sunsets on the beach! Fall in love with the serene bay beach outside your door in this completely renovated and light fi ...

    From $720 per night (USD)

    VRBO

    Details
  • CHARMING COTTAGE NEAR OCEAN BEACHES, FARM STAND, TRAIN & VILLAGE - RR#: 22-517
    From $670 per night (USD)

    Expedia

    CHARMING COTTAGE NEAR OCEAN BEACHES, FARM STAND, TRAIN & VILLAGE - RR#: 22-517

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    4

    Charming and cozy East Hampton cottage on a beautifully and privately landscaped half acre adjacent to farm fields. It o ...

    From $670 per night (USD)

    Expedia

    Details
  • Quaint DT Greenport Apt - 2 Mi to Shelter Island!
    From $286 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 $286 per night (USD)

    VRBO

    Details
  • Book your vacation at our EH retreat on the water!
    From $1810 per night (USD)

    Expedia

    Book your vacation at our EH retreat on the water!

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Escape the hustle and bustle of the city... And enjoy a relaxing getaway to our peaceful retreat in the hamptons. Our ...

    From $1810 per night (USD)

    Expedia

    Details
  • Southampton Village Renovated Sun-filled Charming Home, Heated Salt water Pool
    From $1732 per night (USD)

    VRBO

    Southampton Village Renovated Sun-filled Charming Home, Heated Salt water Pool

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    10

    The home has four bedrooms, three full bathrooms with an open living room and sitting room (with flat screen tv on the w ...

    From $1732 per night (USD)

    VRBO

    Details
  • Center of Town - Ideal for Beach, Golf & Tennis
    From $796 per night (USD)

    VRBO

    Center of Town - Ideal for Beach, Golf & Tennis

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Our home is centrally located in Montauk, just a short walk or bike ride to all that the area has to offer. Disconnect f ...

    From $796 per night (USD)

    VRBO

    Details
  • Bright Apartment - 1\/2 Mi to Greenport Harbor!
    From $414 per night (USD)

    VRBO

    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 $414 per night (USD)

    VRBO

    Details
  • Amazing Rocky Point Retreat Overlooking the Sound!
    From $499 per night (USD)

    Expedia

    Amazing Rocky Point Retreat Overlooking the Sound!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    6

    Take in salty air and seagull song when you stay at 'McFord's on the Sound,' a bright and breezy 3-bedroom, 2-bath house ...

    From $499 per night (USD)

    Expedia

    Details
  • Oasis heaven close to everything you need!
    From $705 per night (USD)

    VRBO

    Oasis heaven close to everything you need!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Oasis pool and landscaping makes it feel like your on a private island. Sunroom with smart TV over looking oasis back ya ...

    From $705 per night (USD)

    VRBO

    Details
  • Aqua by American Beech - Deluxe King
    From $307 per night (USD)

    Expedia

    Aqua by American Beech - Deluxe King

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

    Located in the heart of Long Island’s wine country, Aqua by American Beech is just 1 ½ hours from Manhattan and within 3 ...

    From $307 per night (USD)

    Expedia

    Details
  • Aqua by American Beech - Deluxe with 2 Queen
    Click For Pricing

    VRBO

    Aqua by American Beech - Deluxe with 2 Queen

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

    Located in the heart of Long Island’s wine country, Aqua by American Beech is just 1 ½ hours from Manhattan and within 3 ...

    Click For Pricing

    VRBO

    Details
  • Aqua by American Beech - Superior with 2 Queens
    Click For Pricing

    Expedia

    Aqua by American Beech - Superior with 2 Queens

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

    Located in the heart of Long Island’s wine country, Aqua by American Beech is just 1 ½ hours from Manhattan. More than 5 ...

    Click For Pricing

    Expedia

    Details
  • Aqua by American Beech - Rooftop Suite
    From $424 per night (USD)

    VRBO

    Aqua by American Beech - Rooftop Suite

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    2

    Located in the heart of Long Island’s wine country, Aqua by American Beech is just 1 ½ hours from Manhattan and within 3 ...

    From $424 per night (USD)

    VRBO

    Details
  • Aqua by American Beech - Superior King
    From $307 per night (USD)

    Expedia

    Aqua by American Beech - Superior King

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

    Located in the heart of Long Island’s wine country, Aqua by American Beech is just 1 ½ hours from Manhattan. You can fin ...

    From $307 per night (USD)

    Expedia

    Details
  • Luxurious Waterfront all Season Home with Private Beach
    From $747 per night (USD)

    VRBO

    Luxurious Waterfront all Season Home with Private Beach

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Relax and enjoy your time at this beautiful east end waterfront getaway. This house is located right on the relaxing an ...

    From $747 per night (USD)

    VRBO

    Details
  • Stunning 3 BR \/ 2.5 Bath New Construction Home in East Hampton w\/ In Ground Pool
    From $1580 per night (USD)

    VRBO

    Stunning 3 BR \/ 2.5 Bath New Construction Home in East Hampton w\/ In Ground Pool

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    10

    Conveniently located equidistant to East Hampton and Sag Harbor Villages, this new construction three bedroom, two and a ...

    From $1580 per night (USD)

    VRBO

    Details
  • Bridgehampton gem in private community- 1 mile from the village
    From $2511 per night (USD)

    VRBO

    Bridgehampton gem in private community- 1 mile from the village

    Bedrooms:
    5
    Bathrooms:
    6
    Sleeps:
    10

    BH Rental- 1 mile from BH village (+3 miles to Ocean Beach) nestled in a private enclave. This sunny, spacious, immacula ...

    From $2511 per night (USD)

    VRBO

    Details
  • Beautiful Westhampton Moriches Bay home!
    From $1413 per night (USD)

    Expedia

    Beautiful Westhampton Moriches Bay home!

    Bedrooms:
    5
    Bathrooms:
    4
    Sleeps:
    8

    Secluded shingled beach house south of Montauk highway with water views of Great Moriches Bay. Minutes from town center ...

    From $1413 per night (USD)

    Expedia

    Details
  • Renovated and Spacious Summer Home with Water View on Picturesque Island.
    From $758 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 $758 per night (USD)

    VRBO

    Details
  • NEW LISTING - Newly Renovated Beach Home - Short Walk to Beach and Town
    From $895 per night (USD)

    Expedia

    NEW LISTING - Newly Renovated Beach Home - Short Walk to Beach and Town

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    8

    Newly renovated beach home near everything - most importantly 5 min walk to town and beach. No car necessary, but large ...

    From $895 per night (USD)

    Expedia

    Details
  • Brand New in the Heart of East Hampton Village with Pool
    From $1648 per night (USD)

    VRBO

    Brand New in the Heart of East Hampton Village with Pool

    Bedrooms:
    6
    Bathrooms:
    5
    Sleeps:
    8

    Location, location, location.....once you park in your driveway, vehicle is no longer needed....yes, that's right....thi ...

    From $1648 per night (USD)

    VRBO

    Details
  • East Hampton SOUTH of the HIGHWAY near Ocean & Further Lane
    From $1488 per night (USD)

    Expedia

    East Hampton SOUTH of the HIGHWAY near Ocean & Further Lane

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    6

    IMPORTANT FOR INSTANT BOOKING - RENTER MUST FULLY QUALIFY ACCORDING TO EAST HAMPTON ORDINANCES- ONCE you advise of the p ...

    From $1488 per night (USD)

    Expedia

    Details
  • Hamptonā€™s summer rental w\/pool near beaches
    Click For Pricing

    VRBO

    Hampton’s summer rental w\/pool near beaches

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    6

    This very quiet and secluded 4 bedroom, 2.5 bath is nestled on just shy of one (1) acre and boasts an open floor plan th ...

    Click For Pricing

    VRBO

    Details
  • Updated home in great location with spacious living & outdoor features
    From $1066 per night (USD)

    Expedia

    Updated home in great location with spacious living & outdoor features

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Cayuga Escape Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...

    From $1066 per night (USD)

    Expedia

    Details
  • Authentic Sag harbor post and beam
    Click For Pricing

    VRBO

    Authentic Sag harbor post and beam

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    4

    New 2 bed 3 bath home offers 2 master suites, jacuzzi tub, smart TVs, central air, and a hot tub. This unique property r ...

    Click For Pricing

    VRBO

    Details
  • Spacious beach cottage with private pool, hot tub, outdoor area & amazing suite
    From $1509 per night (USD)

    Expedia

    Spacious beach cottage with private pool, hot tub, outdoor area & amazing suite

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    15 Seneca Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...

    From $1509 per night (USD)

    Expedia

    Details
  • Spacious Dog-Friendly Home with Renovated Kitchen and Bathrooms
    From $993 per night (USD)

    VRBO

    Spacious Dog-Friendly Home with Renovated Kitchen and Bathrooms

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    11

    Baywatch Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired d ...

    From $993 per night (USD)

    VRBO

    Details
  • Access to all the Hamptons has to offer
    From $449 per night (USD)

    VRBO

    Access to all the Hamptons has to offer

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    7

    You will recharge your batteries in the incredible light filled contemporary ranch with 20' cathedral ceilings and 3 co ...

    From $449 per night (USD)

    VRBO

    Details
  • Quiet Family Friendly Hideaway With Pool And Poolhouse
    From $1250 per night (USD)

    VRBO

    Quiet Family Friendly Hideaway With Pool And Poolhouse

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    12

    Wonderful beach house with large open plan living room, kitchen, dining area, den, master suite and two guest bedrooms ...

    From $1250 per night (USD)

    VRBO

    Details
  • Airy Wooden Beach House with Big Private Deck, close to Atlantic Ocean Beach or gentler bay swimming.
    Click For Pricing

    Expedia

    Airy Wooden Beach House with Big Private Deck, close to Atlantic Ocean Beach or gentler bay swimming.

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Large open, high-ceilinged living room surround by four air-conditioned bedrooms, two enclosed porches, large private op ...

    Click For Pricing

    Expedia

    Details
  • Hamptons Getaway With Heated Pool, Har Tru Tennis, Built -in Grill, Bike Shed
    From $846 per night (USD)

    VRBO

    Hamptons Getaway With Heated Pool, Har Tru Tennis, Built -in Grill, Bike Shed

    Bedrooms:
    4
    Bathrooms:
    6
    Sleeps:
    10

    Beautiful, airy, contemporary Quogue home on 1 acre lot along a tree-lined street. Secluded with 6 large bedrooms, 4 b ...

    From $846 per night (USD)

    VRBO

    Details
  • Fall in thešŸŒ…beautiful sunsets
    From $350 per night (USD)

    Expedia

    Fall in the🌅beautiful sunsets

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    3

    Bit of nostalgia at the beach. Lovely one bedroom one full bath suite in 1860 farmhouse surrounded by lovely gardens, sc ...

    From $350 per night (USD)

    Expedia

    Details
  • East Hampton Sag Harbor Village Fringe Pool Hot Tub Gym
    From $3352 per night (USD)

    VRBO

    East Hampton Sag Harbor Village Fringe Pool Hot Tub Gym

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    8

    Welcome to this all brand new 3000 sf beach house with flex 4/5 BR and 3 BA, situated on 3 acres at the end of a private ...

    From $3352 per night (USD)

    VRBO

    Details
  • Walk to the Village! Charming modern farmhouse.
    From $1159 per night (USD)

    Expedia

    Walk to the Village! Charming modern farmhouse.

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Kick back and relax in this calm, stylish space. House in the village but feels like you’re on your own retreat. House i ...

    From $1159 per night (USD)

    Expedia

    Details
  • Affordable Ocean Beach, Fire Island Studio Sleeps 2 max, WiFi, 31\ Smart ROKU TV
    From $525 per night (USD)

    VRBO

    Affordable Ocean Beach, Fire Island Studio Sleeps 2 max, WiFi, 31\" Smart ROKU TV

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Affordable Studio Apartment, Sleeps 2 maximum. 25 and older please. Similar to a large hotel room. Check in 4 PM, Chec ...

    From $525 per night (USD)

    VRBO

    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
  • Walk to town, Bike to beach. Private pool oasis
    From $981 per night (USD)

    VRBO

    Walk to town, Bike to beach. Private pool oasis

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    This home has two bedrooms and one bath and is newly renovated. The main bedroom has a sliding glass door that opens up ...

    From $981 per night (USD)

    VRBO

    Details
  • Mid-June and 4th of July week in the Hamptons
    From $861 per night (USD)

    Expedia

    Mid-June and 4th of July week in the Hamptons

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    The house is situated on a quiet street in a wooded area, 5 minutes walking distance from the Peconic Bay and its beaut ...

    From $861 per night (USD)

    Expedia

    Details
  • Brand new kitchen, Jacuzzi, organic garden, minutes to the Village
    From $1543 per night (USD)

    VRBO

    Brand new kitchen, Jacuzzi, organic garden, minutes to the Village

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    An immaculately maintained contemporary style house with a brand new kitchen, a large pool and and an organic vegetable ...

    From $1543 per night (USD)

    VRBO

    Details
  • Ocean views, Beach Access, Designer Hither Hills House....
    From $2102 per night (USD)

    VRBO

    Ocean views, Beach Access, Designer Hither Hills House....

    Bedrooms:
    6
    Bathrooms:
    5
    Sleeps:
    10

    A captivatingly exceptional property, 46 Edison Drive is the epitome of superior quality and modern luxury, enhanced by ...

    From $2102 per night (USD)

    VRBO

    Details
  • 2025 Ocean Bay Park Booking Now- Beautiful Family Home
    From $747 per night (USD)

    VRBO

    2025 Ocean Bay Park Booking Now- Beautiful Family Home

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    5

    Beautiful Home nestled in the quieter part of Ocean Bay Park Home sleeps 7 Bedroom 1 -king size bed Bedroom 2- 2 twins ...

    From $747 per night (USD)

    VRBO

    Details
  • 2br Private Apt, Pet Pal, Events, LTR, STR, Cozy
    From $161 per night (USD)

    Expedia

    2br Private Apt, Pet Pal, Events, LTR, STR, Cozy

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    8

    Indulge in the luxury of your own private haven with a captivating entrance boasting two dreamy bedrooms—the first adorn ...

    From $161 per night (USD)

    Expedia

    Details
  • Contemporary Beach Cottage - Walk to Bay, Minutes from Ocean
    Click For Pricing

    VRBO

    Contemporary Beach Cottage - Walk to Bay, Minutes from Ocean

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    This recently updated, contemporary cottage is located just steps from the Peconic Bay, and minutes from beautiful Ponqu ...

    Click For Pricing

    VRBO

    Details
  • Shelter Island Retreat With Pool ...A Stone's Throw Away From The Beach!
    From $711 per night (USD)

    Expedia

    Shelter Island Retreat With Pool ...A Stone's Throw Away From The Beach!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    7

    * Please Read House Rules And Policy's Before Booking* Perfect For Families!! Dogs Welcome! Located within close proxim ...

    From $711 per night (USD)

    Expedia

    Details
  • Gorgeous Southampton Contemporary country charm
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    VRBO

    Gorgeous Southampton Contemporary country charm

    Bedrooms:
    5
    Bathrooms:
    4
    Sleeps:
    8

    Newly renovated exterior home in Southampton. 7 minutes from Southampton Village and 10 minutes from Coopers Beach. Walk ...

    Click For Pricing

    VRBO

    Details
  • Private Beach Vacation Home- steps from shore, sleeps 12  \nRR Cert. No. 24-291
    From $1526 per night (USD)

    Expedia

    Private Beach Vacation Home- steps from shore, sleeps 12 \nRR Cert. No. 24-291

    Bedrooms:
    5
    Bathrooms:
    7
    Sleeps:
    14

    Located steps from pristine private ocean beach (1/16th of a mile), this home has it all. Resident can walk or drive to ...

    From $1526 per night (USD)

    Expedia

    Details
  • Charming Modern house close to East Hampton town center
    From $937 per night (USD)

    VRBO

    Charming Modern house close to East Hampton town center

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    available on monthly basis; Summer 2022. ideal summer getaway in the Hamptons; 2 bed, 1 bath, modern ; newly renovated ...

    From $937 per night (USD)

    VRBO

    Details
  • Ocean Beach Getaway
    From $721 per night (USD)

    Expedia

    Ocean Beach Getaway

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Enjoy this classic beach house with modern updates in the center of Ocean Beach. Everything you need to enjoy a day at ...

    From $721 per night (USD)

    Expedia

    Details
  • Historical Bed and breakfast<br>
    From $3768 per night (USD)

    VRBO

    Historical Bed and breakfast<br>

    Bedrooms:
    6
    Bathrooms:
    6
    Sleeps:
    12

    Built in 1690, newly restored. Located in Watermill the center of the Hamptons. Restaurants and shopping right around th ...

    From $3768 per night (USD)

    VRBO

    Details
  • Bayfront home with private path across the street to ocean, pool and hot...
    From $2238 per night (USD)

    VRBO

    Bayfront home with private path across the street to ocean, pool and hot...

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Please note that a reservation for this property needs to be approved before it is confirmed. Westhampton Bayfront Oasi ...

    From $2238 per night (USD)

    VRBO

    Details
  • STUNNING MODERN RE-CONSTRUCTED BARN, SHORT BIKE OR WALK TO VILLAGE AND BEACHES
    Click For Pricing

    VRBO

    STUNNING MODERN RE-CONSTRUCTED BARN, SHORT BIKE OR WALK TO VILLAGE AND BEACHES

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    10

    This incredible property was completely re-built in 2014 over the footprint of the original Ludlow Grange Barn. Cool and ...

    Click For Pricing

    VRBO

    Details
  • Westhampton Beach Resort Waterfront, Pool, Tennis
    From $2161 per night (USD)

    VRBO

    Westhampton Beach Resort Waterfront, Pool, Tennis

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    10

    Don’t get caught in single lane traffic! Beautifully located fast commute from NYC. First Hamlet off 27 Situated 2.5 m ...

    From $2161 per night (USD)

    VRBO

    Details
  • Adorable Cottage with Water Views, Across the street from Prime & other eateries
    From $345 per night (USD)

    VRBO

    Adorable Cottage with Water Views, Across the street from Prime & other eateries

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    This unique cottage offers seclusion and comfort located just across the street from the beautiful Huntington Harbor. It ...

    From $345 per night (USD)

    VRBO

    Details
  • East Hampton Cottage
    Click For Pricing

    Expedia

    East Hampton Cottage

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Magical summer garden opens up to a neighboring horse farm with sunset views from the kitchen and outdoor dining areas. ...

    Click For Pricing

    Expedia

    Details
  • Private Community Ranch
    Click For Pricing

    VRBO

    Private Community Ranch

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Comfortable 3 bedroom ranch located in a great private beach community in East Quogue. Located across Tiana Bay from Dun ...

    Click For Pricing

    VRBO

    Details
  • Spacious Hamptons Apartment - Below Ground Level
    From $316 per night (USD)

    Expedia

    Spacious Hamptons Apartment - Below Ground Level

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    2

    Book your stay at this spacious, modern, and charming 2-bedroom apartment. Located within walking distance of the Long I ...

    From $316 per night (USD)

    Expedia

    Details
  • Newly built ranch, beautifully landscaped with pool, large yard, patio,...
    From $606 per night (USD)

    VRBO

    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 $606 per night (USD)

    VRBO

    Details
  • End of Cul De Sac Nice Bike Ride to Main Beach on back roads. Pond Setting.
    From $1460 per night (USD)

    Expedia

    End of Cul De Sac Nice Bike Ride to Main Beach on back roads. Pond Setting.

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    10

    East Hampton Rental registry #24-937 thoroughly cleaned house with low rental turnover. House mostly used by owner. E ...

    From $1460 per night (USD)

    Expedia

    Details
  • WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr
    From $939 per night (USD)

    VRBO

    WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr

    Bedrooms:
    5
    Bathrooms:
    6
    Sleeps:
    12

    SUMMER 2025 DATES NOW OPEN - June 22nd to Labor Day are usually one week or more rentals with check-in and out on Satur ...

    From $939 per night (USD)

    VRBO

    Details
  • Wainscott Hamlet
    From $2000 per night (USD)

    Expedia

    Wainscott Hamlet

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    6

    Beautiful private home gives you a resort feel with midcentury flair. Lounge and dine under cover in the 44 ft. long co ...

    From $2000 per night (USD)

    Expedia

    Details
  • Family Beach house - steps from the water!
    From $1014 per night (USD)

    VRBO

    Family Beach house - steps from the water!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    6

    Soak up summer and stay at this centrally located, family-friendly beach house. Whether you take a 3 minute walk to the ...

    From $1014 per night (USD)

    VRBO

    Details
  • Newly renovated 5mins walk from best surf beach Ditch!
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    Expedia

    Newly renovated 5mins walk from best surf beach Ditch!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    6

    Cozy newly-renovated home for your summer getaway. 6 guests can comfortably share 3 bedrooms, 2 full bathrooms and an ou ...

    Click For Pricing

    Expedia

    Details
  • Sag Harbor Summer Fun
    Click For Pricing

    VRBO

    Sag Harbor Summer Fun

    Bedrooms:
    8
    Bathrooms:
    7
    Sleeps:
    12

    Sag Harbor (7 bedroom/8.5 bathroom) recently renovated home for rent: 3 bedrooms w/ ensuite bathrooms and 2 bedrooms sh ...

    Click For Pricing

    VRBO

    Details
  • Summer in the Hamptons
    From $885 per night (USD)

    Expedia

    Summer in the Hamptons

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to summer on Sunset Ave in Westhampton Beach. Situated on ½ acre, this 3-bedroom newly renovated home has all th ...

    From $885 per night (USD)

    Expedia

    Details
  • North Fork Oasis: Heated Pool, Hot tub
    From $1254 per night (USD)

    VRBO

    North Fork Oasis: Heated Pool, Hot tub

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    9

    Summary: This is a consummate North Fork Oasis. When you arrive, you are greeted by a grand entrance with a wrap-around ...

    From $1254 per night (USD)

    VRBO

    Details
  • Waterfront Beach House on Beautiful Shinnecock Bay
    Click For Pricing

    Expedia

    Waterfront Beach House on Beautiful Shinnecock Bay

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Bayfront Sandy Beach House on beautiful Shinnecock Bay with views to Dune Road. Kayak, Paddleboard, fish, swim or sunba ...

    Click For Pricing

    Expedia

    Details
  • Fantastic Family & Friends Getaway Montauk House - Any Season!
    From $957 per night (USD)

    VRBO

    Fantastic Family & Friends Getaway Montauk House - Any Season!

    Bedrooms:
    5
    Bathrooms:
    6
    Sleeps:
    14

    Incredibly spacious and beautiful five bed and five bathroom home located in the heart of Montauk offers pond and partia ...

    From $957 per night (USD)

    VRBO

    Details
  • HAMPTONS GETAWAY FOR 2 - STUDIO APARTMENT
    Click For Pricing

    Expedia

    HAMPTONS GETAWAY FOR 2 - STUDIO APARTMENT

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    NEW VACATION RENTAL Studio (270 sq) - EH Springs Bay Area Located in a Beautiful Newly Renovated Ranch Style House Grea ...

    Click For Pricing

    Expedia

    Details
  • Elegant East Hampton Estate nestled on nearly 5 acres of land, stunning...
    From $1532 per night (USD)

    VRBO

    Elegant East Hampton Estate nestled on nearly 5 acres of land, stunning...

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    9

    Magnificent on Mile Hill Elegant East Hampton Estate nestled on nearly 5 acres of land, stunning infinity pool, integra ...

    From $1532 per night (USD)

    VRBO

    Details
  • Relax in Hampton Bays...
    From $648 per night (USD)

    Expedia

    Relax in Hampton Bays...

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    'Architecturally bright, airy & open floor plan. Newly built, contemporary amenities.' Location: Hampton Bays, Hamptons ...

    From $648 per night (USD)

    Expedia

    Details
  • Spacious home with renovated kitchen, large deck, & tennis
    From $457 per night (USD)

    VRBO

    Spacious home with renovated kitchen, large deck, & tennis

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Wilmot Escape Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...

    From $457 per night (USD)

    VRBO

    Details
  • PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH
    From $948 per night (USD)

    Expedia

    PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH

    Bedrooms:
    6
    Bathrooms:
    4
    Sleeps:
    10

    Enjoy the beauty of being in East Hampton! Our luxurious vacation rental boasts a resort like back yard featuring a mass ...

    From $948 per night (USD)

    Expedia

    Details
  • Charming English Tudor
    From $1600 per night (USD)

    VRBO

    Charming English Tudor

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    This spacious and charming 4,500 square foot English Tudor is situated on 2.25 acres in Southold. It has 4 bedrooms, 3 b ...

    From $1600 per night (USD)

    VRBO

    Details
  • Charming Modern Home - Winter and Summer Retreat
    From $875 per night (USD)

    Expedia

    Charming Modern Home - Winter and Summer Retreat

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    9

    Beautiful home on a quiet street. Immaculately maintained. Summer and winter retreat. In addition to five bedrooms and t ...

    From $875 per night (USD)

    Expedia

    Details