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 PricingExpedia
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
Click For PricingVRBO
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
Click For PricingVRBO
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
Click For PricingExpedia
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
Click For PricingExpedia
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
Click For PricingVRBO
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
Click For PricingExpedia
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
Click For PricingExpedia
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 PricingVRBO
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 PricingVRBO
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 PricingVRBO
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
Click For PricingExpedia
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 PricingVRBO
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 PricingExpedia
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 PricingExpedia
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 PricingVRBO
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 PricingExpedia
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 PricingExpedia
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 PricingVRBO
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