
Southold Rentals

- From $483 per night (USD)
VRBO
Between the Vineyard and Sea. Walk to sandy beach from this charming cottage.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to our charming 3-bedroom vacation home in the heart of Southold, where you can immerse yourself in the beauty of ...
From $483 per night (USD)VRBO
- Click For Pricing
Expedia
The perfect north fork experience
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
Our home is on a 10 acre private field surrounded by beaches, farms and local wineries. We have a large fenced pool with ...
Click For PricingExpedia
- From $1674 per night (USD)
VRBO
Truly special! Huge North Fork Villa Great for multiple families- Walk to beach
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
This stunning luxury home is everything you could possibly want in a vacation rental! -6 Bedrooms -4 Bathrooms -Huge 2 ...
From $1674 per night (USD)VRBO
- From $643 per night (USD)
VRBO
NorthFork Serenity, next to beach and wineries
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
A stones throw to your private creek entrance or an 8 minute walk down a private road to the exceptional Goose Creek Bea ...
From $643 per night (USD)VRBO
- From $1200 per night (USD)
VRBO
Southold Waterfront with Boat Dock, Boat Ramp, Hot Tub & Beaches
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy the beauty of Long Island's North Fork right here at our vacation house in Southold. Enjoy fabulous water views, ...
From $1200 per night (USD)VRBO
- From $523 per night (USD)
VRBO
2 Bedroom Apartment in Historic Home with private yard (WBH)
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Calendar NOT always up to date check for availability Beach Parking good at all Southold Town Beaches Pass INCLUDED fr ...
From $523 per night (USD)VRBO
- From $1216 per night (USD)
VRBO
Beachfront - endless sunsets, sandy beach, cozy sunroom & open concept kitchen
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Nestled on the water, this 3-bedroom, 2 1/2 bath house is a bright and open space perfect for creating unforgettable mem ...
From $1216 per night (USD)VRBO
- From $1088 per night (USD)
VRBO
One block from the beach!!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Available August - Labor Day 2021!! $30,000.00 Take a long walk on the beach or set sail in Southold Bay for Shelter I ...
From $1088 per night (USD)VRBO
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VRBO
Enjoy Wine Country and Walk The Beautiful Beach At Sunset
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
* 10 min walk to neighborhood sandy beach! * 5 min walk to vineyard with tasting room. Spacious Contemporary home. ...
Click For PricingVRBO
- From $1132 per night (USD)
VRBO
Beautiful waterfront house in Southold
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Beautiful Waterfront Home With Stunning Views of Hashamomuck Pond. Escape from it all for a memorable family vacation in ...
From $1132 per night (USD)VRBO
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VRBO
Enjoy Wine Country and Take Walks On Beautiful, Solitary beaches At Sunset
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
* 10 min walk to neighborhood sandy beach * 5 min walk to vineyard with tasting room. Spacious Contemporary home. Ma ...
Click For PricingVRBO
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Expedia
New home with open floor plan located close to wineries and Greenport
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful home located near the water. 4 bedroom, 3 bathroom open floor plan built in 2019. Very close to wineries, Gree ...
Click For PricingExpedia
- From $309 per night (USD)
VRBO
Charming house walking distance from beautiful Kenney’s Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Experience the North Fork in our bright, happy home in the heart of wine country, just steps from beautiful Kenney's Bea ...
From $309 per night (USD)VRBO
- From $1053 per night (USD)
VRBO
Unique Southold waterfront luxury home with heated pool on Long Creek
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
We bought our wonderful house five years ago and have made many important renovations. The newest is a hybird bocce cour ...
From $1053 per night (USD)VRBO
- From $527 per night (USD)
VRBO
Cute Cottage Apartment Near town, beaches and vineyards (WBH)
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Calendar NOT always up to date check for availability Beach Parking good at all Southold Town Beaches Pass INCLUDED fr ...
From $527 per night (USD)VRBO
- From $444 per night (USD)
Expedia
House of Classic Arts and Crafts North Fork
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This charming Southold village house sits on a half acre with a back deck overlooking a sweeping backyard. Newly furnish ...
From $444 per night (USD)Expedia
- From $917 per night (USD)
VRBO
Modern North Fork Retreat with massive pool and Private Beach Access
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Newly built farmhouse-style retreat with in-ground pool and private beach access in the heart of the North Fork. This lo ...
From $917 per night (USD)VRBO
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Expedia
Two minuet walk to the beach. On a quiet private road
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Located in the north forks famous wine district. Can sleep up to five. Eat in glassed/screened front porch faces the sou ...
Click For PricingExpedia
- From $383 per night (USD)
VRBO
Architect-Renovated, Pristine Ranch, Modern Kitchen, Short Walk to Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Completely renovated 60's ranch, 2 bedrooms with queen sleeper sofa in family room to sleep 6, new appliances, washer/dr ...
From $383 per night (USD)VRBO
- From $1131 per night (USD)
VRBO
Sun-Filled 4-BR Home, North Fork - amid Dunes, Beach & Spectacular Sunsets. 3-BA
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
We fell in love with this inlet, this neighborhood, this beach, these dunes, and this home the first time we visited in ...
From $1131 per night (USD)VRBO
- From $839 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 $839 per night (USD)VRBO
- From $1215 per night (USD)
VRBO
North Fork Family Villa- large family home with fenced in pool
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Grand Beach Home, Room For Family and guests. 5 BR, 3.5 BA, Radiant Heat, Gourmet Kitchen With gas Wolf Stove. 10 Foot ...
From $1215 per night (USD)VRBO
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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 PricingVRBO
- From $937 per night (USD)
Expedia
Gorgeous Historical 6 bdrm House close to vineyards and breweries,
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
This property is a newly renovated historical Victorian House built in the late 1800's. Each room is furnished with hand ...
From $937 per night (USD)Expedia
- From $791 per night (USD)
VRBO
North Fork Waterfront + Private beaches + Spectacu
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Completely renovated in the last two years with new kitchen, two and a half new bathrooms, one with jetted tubs and bot ...
From $791 per night (USD)VRBO
- From $923 per night (USD)
VRBO
Privacy!! Heated salt-water pool, central a\/c, all kinds of families welcome
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
NO BETTER PLACE TO ENJOY THE BEST OF THE NORTH FORK Due to the utmost care for your family and mine during the worst of ...
From $923 per night (USD)VRBO
- From $860 per night (USD)
VRBO
Shelter Island Waterfront Home!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
A water front home with magnificent Shelter Island Sound views from the entire main area, including living room, porch, ...
From $860 per night (USD)VRBO
- From $1411 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 $1411 per night (USD)VRBO
- From $235 per night (USD)
VRBO
Sweet Southold Beach Cottage<br> FALL WINTER SUMMER
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Sweet Southold Beach Cottage Spring/Summer/Fall/Winter Prime location! View Peconic Bay from your driveway! One minute ...
From $235 per night (USD)VRBO
- From $740 per night (USD)
VRBO
North Fork Sound Front Beach House
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Designed by renowned architects Abercrombie & Vieyra for their private use, this 4 bedroom, sound front home with a priv ...
From $740 per night (USD)VRBO
- From $282 per night (USD)
VRBO
WALK TO BEACH - Founders Landing, Southold - restaurants, Village, Jitney, LIRR
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
BEAUTIFUL North Fork Just renovated cottage in Founders Landing Beach Community in Historic Southold Village - - very s ...
From $282 per night (USD)VRBO
- From $309 per night (USD)
VRBO
Cottage on private road and 5-min walk to beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Perfect all-season cottage with easy access to beaches, wineries, restaurants, and all the great things the North Fork h ...
From $309 per night (USD)VRBO
- From $705 per night (USD)
VRBO
Wineries, Apple Picking, Pumpkin Picking, Outdoor Restaurants and Beaches!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Spacious home great layout for work or school from home. Featured 3-4 bedrooms, 3.5 baths, CAC, hardwood floors, gourmet ...
From $705 per night (USD)VRBO
- From $651 per night (USD)
Expedia
Waterfront, private beach, ready for adventure, light & bright!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Set on a magical one-acre promontory, jutting into beautiful Long Creek with spectacular water views from every room, th ...
From $651 per night (USD)Expedia
- From $522 per night (USD)
VRBO
Bright light, water views, steps from the beach!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
On a quiet peninsula in Southold, this house has everything you need for a North Fork summer or cozy off season. It's fu ...
From $522 per night (USD)VRBO
- From $1034 per night (USD)
VRBO
Beautifully appointed waterfront property with heated pool and cabana
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Guests are sure to enjoy a memorable vacation in this fully furnished,4 bedroom 3 bath property. ( The 3rd bathroom is ...
From $1034 per night (USD)VRBO
- From $582 per night (USD)
VRBO
Steps from Cedar Beach ! Tranquil Retreat in the Heart of Wine Country
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Steps from Peconic Bay and Cedar beach. Stay in our Southold home in the heart of North Fork and enjoy the best the No ...
From $582 per night (USD)VRBO
- From $506 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 $506 per night (USD)VRBO
- From $627 per night (USD)
VRBO
Shelter Bay Cove Waterfront + Beach + spectacular
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 7
Lovingly restored with new kitchen, refinished hardwood floors throughout, two full modern bathrooms, open fireplace, ce ...
From $627 per night (USD)VRBO
- From $566 per night (USD)
VRBO
Private Coastal Two Bedroom Cottage on the Water
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
A coastal cottage on the water surrounded by vineyards and farm stands on the North Fork. Unwind in the backyard with a ...
From $566 per night (USD)VRBO
- From $712 per night (USD)
VRBO
Water View Beach House just steps to Private Sandy Beach!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Just steps from a private sandy beach with a beautiful view across the Peconic Bay to Sag Harbor and perfect sunsets. Ho ...
From $712 per night (USD)VRBO
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Expedia
Private beach house and Long Island sound views, North Fork
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
This two bedroom home sits on a lush bluff overlooking the Long Island sound in the North Fork. The guest house with a l ...
Click For PricingExpedia
- From $2018 per night (USD)
VRBO
One Of A Kind, Resort- Like Waterfront Cottage In Wine Country
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
LI Sound Waterfront Cottage with 2 Bedrooms and 1 Bathroom. Completely Renovated and Modern Living Space with Open Layou ...
From $2018 per night (USD)VRBO
- From $590 per night (USD)
Expedia
Sea Breeze Paradise: Beachfront & Panoramic Views
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Sea Breeze Paradise is a newly renovated home. A paradise for those of you who want to enjoy the sun and fresh air with ...
From $590 per night (USD)Expedia
- From $780 per night (USD)
VRBO
Farmhouse Retreat
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Experience the perfect blend of tranquility and convenience at our zen farmhouse. Nestled close to stunning beaches and ...
From $780 per night (USD)VRBO
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Expedia
Water views Beach and pool!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Spacious entertainment, relax by the fireplace or relax in the closed porch , Private Beach on the corner of property. E ...
Click For PricingExpedia
- From $1126 per night (USD)
VRBO
Renovated American Farmhouse in the heart of Southold with heated saltwater pool
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Our newly renovated Farmhouse is centrally located in Southold with easy access by bus, train or car. Enjoy your mornin ...
From $1126 per night (USD)VRBO
- From $539 per night (USD)
VRBO
Charming Northfork home.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This house is newly updated, beautifully furnished and comfortable. It is light and spacious with hard wood floors throu ...
From $539 per night (USD)VRBO
- From $673 per night (USD)
VRBO
Luxury by the Sea
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Your search 👀 is over! Brand New 🔨 Construction. Charming, luxurious, private, comfortable Beach 🏖 House. Stunning ...
From $673 per night (USD)VRBO
- From $378 per night (USD)
VRBO
3 Br North Fork Getaway In Private Beach Community
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Newly decorated beach house near vineyards on the North Fork. Just steps from a private beach on tranquil Goose Creek. ...
From $378 per night (USD)VRBO
- From $504 per night (USD)
VRBO
Great Location!! Walk to Town & Train!!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This is a truly unique and beautifully finished historic farmhouse that is comfortable and charming. You can walk to th ...
From $504 per night (USD)VRBO
- From $497 per night (USD)
VRBO
Lovely, Serene and Stylish Country Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
This perfectly placed home is minutes from all that's great about the North Fork: loads of beaches, excellent wineries, ...
From $497 per night (USD)VRBO
- From $1697 per night (USD)
VRBO
Luxurious Estate with Pool by Kenney's Beach, McCabe's Beach and Horton's Point
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 12
This 6 bedroom estate is situated in Southold, NY, within 10 minutes walking distance of Kenney's and McCabe's beaches. ...
From $1697 per night (USD)VRBO
- From $599 per night (USD)
VRBO
Goose Creek Getaway: Modern Home with Beach Access
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Summary: Goose Creek Getaway is a beautifully remodeled 3-bedroom, 2 full baths North Fork vacation home just a 1-minute ...
From $599 per night (USD)VRBO
- Click For Pricing
VRBO
Stunning Home & Private Beach on the North Fork
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to a slice of Heaven on the pastoral North Fork. Jaw dropping views, visible from almost every room in the house ...
Click For PricingVRBO
- From $701 per night (USD)
Expedia
Heated pool on Goose Creek, private dock, massive yard walk to beach, wineries
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 7
Southold Permit # 0361. Pool opens Mid April! One season off of a full renovation - reviews before 2022 are from befo ...
From $701 per night (USD)Expedia
- Click For Pricing
VRBO
The North Fork Loft
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
Spectacular Waterfront Loft in the heart of The North Forks' Wine Country. Enjoy the tranquil setting at this waterfront ...
Click For PricingVRBO
- From $553 per night (USD)
VRBO
Cottage by Cedar Beach
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 5
Cute as a button cottage with 2 bedrooms and 1.5 bath. Oversized outside patio with large teak dining table and huge con ...
From $553 per night (USD)VRBO
- Click For Pricing
VRBO
The Stucco House
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Very unique style house in the area. Updated with newly Gut renovated bathroom and new appliances. Large enclosed porch ...
Click For PricingVRBO
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Expedia
Seaside Southold Escape in Private Beach Community
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
There's nothing like fall on the North Fork! Bonfires on the beach, apple & pumpkin picking, corn mazes, vineyards, and ...
Click For PricingExpedia
- Click For Pricing
VRBO
Cozy Cottage on North Fork
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Cozy Cottage. Great Location and nice yard with BBQ and rear deck. Fully furnished Site says I have to have 96 more le ...
Click For PricingVRBO
- From $640 per night (USD)
VRBO
Salt & Sea House - beaches, wineries, farms nearby
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Escape to the Salt & Sea House! Embrace the tranquility of our spacious 3 bedroom, 3 bathroom home nestled on a private ...
From $640 per night (USD)VRBO
- From $1013 per night (USD)
VRBO
Waterfront, New Construction North Fork Beach House
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Waterfront (with dock) beach house located on Goose Creek, Southold (North Fork, LI). This custom-built new construction ...
From $1013 per night (USD)VRBO
- From $1652 per night (USD)
Expedia
5 Bedrooms ~ Steps from a Private Sandy Beach and Beautiful Vineyard Views..
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Guests are sure to enjoy a memorable vacation in this fully furnished, 5 bedroom/3.5 bath newly renovated expansive mode ...
From $1652 per night (USD)Expedia
- From $880 per night (USD)
VRBO
Family and dog-friendly getaway near amazing wineries, beaches and restaurants!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to the NOFO—where you'll be greeted by beautiful beaches, dozens of wineries and some of the best cuisine New Yo ...
From $880 per night (USD)VRBO
- From $205 per night (USD)
Expedia
Kid-Friendly Home near the Ocean with Private Gas Grill, Fast WiFi, and Cable
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Classic Southold Country Charmer Our calendar is updated in real-time & our nightly rates are accurately displayed. Sim ...
From $205 per night (USD)Expedia
- From $857 per night (USD)
VRBO
Kenneys Beach retreat by the Wineries
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
This 3 bedroom 2 bathroom Ranch with open floor plan is just a short distance to one of the nicest and sandiest beaches ...
From $857 per night (USD)VRBO
- From $613 per night (USD)
Expedia
Private Waterfront Home: Dock, Kayaks
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Private Waterfront Home is a beautiful home located on the North Fork of Long Island, it has a Master bedroom ...
From $613 per night (USD)Expedia
- From $366 per night (USD)
VRBO
Lovely Cottage in the Heart of Long Island Wine country
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Peaceful pondfront cottage with two bedrooms , 1 1/2 baths, pull out couch in Living room can sleep two more , and love ...
From $366 per night (USD)VRBO
- From $588 per night (USD)
Expedia
Southold, NY- Heart of North Fork Wine Country
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
This is a Spacious & Meticulous Cape On Great Hogs Neck Peninsula ~ This Charming 4-Plus Bedroom 3.5 Bath Expanded Cape ...
From $588 per night (USD)Expedia
- From $1042 per night (USD)
VRBO
Water front beach house w\/ private beach with 3 bedrooms\/2 bathrooms\/Large Deck
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
In the picturesque seaside village of Greenport, this ocean-view three-bedroom retreat provides a peaceful and refreshin ...
From $1042 per night (USD)VRBO
- Click For Pricing
Expedia
Cozy Retreat surrounded by Wine Country and Beach Sunsets
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
This retreat is the ultimate country escape. The house has a spacious living space perfect for entertaining or kids. T ...
Click For PricingExpedia
- From $2706 per night (USD)
VRBO
Panoramic Water Views, plunge pool, hot tub, fire pit & walk to beach
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 11
*Soake Plunge Poll Under Constriction - ready for June 2025! Perfect share house as all bedrooms have en-suite bathroom ...
From $2706 per night (USD)VRBO
- Click For Pricing
Expedia
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 PricingExpedia
- Click For Pricing
VRBO
Private Beach community home nestled in the heart of Long Island's North Fork
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Located in the Bay Haven Beach Community with large sandy beach, park area on the water, covered picnic area and a consi ...
Click For PricingVRBO
- Click For Pricing
Expedia
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 PricingExpedia
- From $796 per night (USD)
VRBO
3 Bedroom NoFo Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy the best the North Fork has to offer while staying at our tranquil and peaceful home! Our 3 bedroom, 2 bathroom ho ...
From $796 per night (USD)VRBO
- From $251 per night (USD)
Expedia
Charming home with fireplace, kayaks, patio, fast WiFi, & washer\/dryer-dogs ok
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Minnehaha Marvel Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $251 per night (USD)Expedia
- From $703 per night (USD)
VRBO
Southold Soundfront Private Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Two bedroom PERFECT beach house located on a private beach. If you love the beach, fishing, swimming and sunsets in a qu ...
From $703 per night (USD)VRBO
- Click For Pricing
Expedia
Cute and simple summer cottage
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Tucked in a shady private road in the heart of the North Fork wine district with access to the white sandy beach of the ...
Click For PricingExpedia
- From $1097 per night (USD)
VRBO
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 $1097 per night (USD)VRBO
- From $603 per night (USD)
Expedia
Peconic Sound Beach Home: Backyard & Vineyards
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Summary: Peconic Sound Beach Home in Peconoc Southold is a quaint beach cottage that has a charming allure. Enjoy your a ...
From $603 per night (USD)Expedia
- From $453 per night (USD)
VRBO
Steve's Place: Heated Pool, 3BR Southold Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Steve's Place is a beautifully and professionally decorated 3-bedroom with 1.5 bathrooms, North fork vacation h ...
From $453 per night (USD)VRBO
- From $3109 per night (USD)
VRBO
HEATED POOL waterfront HOT TUB, GYM, Watersports, BOATER DELIGHT luxury modern
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 14
Brand new heated gunite saltwater pool!!!! A sparkling clean and modern 6 bedroom, 4 bath waterfront home offering all t ...
From $3109 per night (USD)VRBO
- From $536 per night (USD)
VRBO
Historic 2-bedroom upstairs apartment close to beaches, town and vineyards.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Great location close to all the North Fork has to offer. The entire upstairs of an Historic Home built in the 1830's wi ...
From $536 per night (USD)VRBO
- From $331 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 $331 per night (USD)VRBO
- Click For Pricing
VRBO
A Natural Getaway
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to a family-fun, pet-friendly house (Rental permit 0343) built in 2019 on a woodsy acre-plus. The home is a stro ...
Click For PricingVRBO
- From $828 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 $828 per night (USD)VRBO
- From $864 per night (USD)
VRBO
Shorecrest Beach House + Beach Front + Ocean views
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
The Shorecrest beach house is located on a grassy bluff overlooking the waters of the Long Island Sound with its own pri ...
From $864 per night (USD)VRBO
- From $452 per night (USD)
VRBO
Southold home at Kenney's Beach 4 bedrooms
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Lovely, spacious home with open, airy floor plan, featuring four bedrooms at Kenney's beach in Southold. First floor has ...
From $452 per night (USD)VRBO
- From $560 per night (USD)
VRBO
Located in the heart of wine country\/BEACHES\/shops.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Historical home full of charm. A home built in the 1700's this home maintains the historical feel with all the amenitie ...
From $560 per night (USD)VRBO
- From $818 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 $818 per night (USD)VRBO
- From $520 per night (USD)
VRBO
Fabulous Waterfront Property in the Heart of Wine Country
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
The beauty of this newly remodeled house in the heart of wine country is unparalleled on the North Fork. Pull up to the ...
From $520 per night (USD)VRBO
- From $468 per night (USD)
VRBO
Beautiful Southold Home with a Water View - 3 Bedroom, 2.5 Bath, Sleeps 8
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
My home is a hidden gem tucked away in a beautiful and quiet neighborhood in Southold, NY. With beautiful water views an ...
From $468 per night (USD)VRBO
- From $477 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 $477 per night (USD)VRBO
- From $529 per night (USD)
VRBO
The Cottage at Sunset Bluff
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This newly renovated charming cottage is sure to spark your romantic side. Located just steps away from the Long Island ...
From $529 per night (USD)VRBO
- From $1024 per night (USD)
VRBO
Perfect Waterfront Family Vacation Home next to the best vineyards in NY!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Completely renovated 3 bedroom, 2 bath Beachfront Cottage. Step outside and enjoy outdoor dining, playing games on th ...
From $1024 per night (USD)VRBO
- From $695 per night (USD)
VRBO
Beautiful Soundfront condominium
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Beautiful 2 bedroom 2 bathroom direct sound front condo in greenport at Cliffside resort direct view. heated pool, beac ...
From $695 per night (USD)VRBO
- From $1061 per night (USD)
VRBO
Southold Escape with Large Saltwater Pool on Wine Trail
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
3 bedroom, 2.5 bathroom home on a 0.55 acre property with large pool and outdoor deck in enclosed private backyard. Bran ...
From $1061 per night (USD)VRBO
- From $560 per night (USD)
VRBO
NF Wine Country Retreat with Dock
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Enjoy this idyllic family friendly home in the heart of North Fork, Long Island. It's a newly renovated and spacious 4 b ...
From $560 per night (USD)VRBO