Southold Rentals
From $673 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 $673 per night (USD)VRBO
From $1501 per night (USD)Expedia
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 $1501 per night (USD)Expedia
From $1157 per night (USD)VRBO
Luxury North Fork Beachfront Escape Near Greenport
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Wake up to breathtaking waterfront views and the soothing sound of waves just steps from your door. This beautifully ren ...
From $1157 per night (USD)VRBO
From $1151 per night (USD)VRBO
One block from the beach!!
- Bedrooms:
- 3
- 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 $1151 per night (USD)VRBO
From $360 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 $360 per night (USD)VRBO
From $643 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 $643 per night (USD)VRBO
From $480 per night (USD)VRBO
House of Classic Arts and Crafts North Fork
- Bedrooms:
- 1
- 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 $480 per night (USD)VRBO
From $942 per night (USD)Expedia
Bayfront Vacation Home in Southold, 5 Bedrooms
- Bedrooms:
- 3
- 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 $942 per night (USD)Expedia
From $1061 per night (USD)VRBO
Gorgeous Historical 6 bdrm House close to vineyards and breweries,
- Bedrooms:
- 4
- 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 $1061 per night (USD)VRBO
From $849 per night (USD)Expedia
Sunset Cottage - Waterfront Beach House on Shelter Bay with Private Dock
- 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 both ...
From $849 per night (USD)Expedia
From $963 per night (USD)VRBO
Beautiful salt water pool and tiki bar! Walk to the beach and Southold town!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This lovely 4BR, 2 bathroom home in Founders Landing is perfect for a family getaway any time of year. The four large ...
From $963 per night (USD)VRBO
From $710 per night (USD)VRBO
Modern & Spacious, Heated Pool, Kenneys Beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Newly appointed spacious retreat near Kenney's Beach, wineries and Southold town, featuring 4 bedrooms and 3 baths sleep ...
From $710 per night (USD)VRBO
From $177 per night (USD)VRBO
Sweet Southold Beach Cottage FALL WINTER SPRING SUMMER 1 min walk to beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Sweet Southold Beach Cottage Spring/Summer/Fall/Winter Prime location! View Peconic Bay from your driveway! One minute ...
From $177 per night (USD)VRBO
From $1041 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 $1041 per night (USD)VRBO
From $399 per night (USD)VRBO
WALK TO BEACH - Founders Landing, Southold - restaurants, Village, Jitney, LIRR
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
BEAUTIFUL North Fork Just renovated cottage in Founders Landing Beach Community in Historic Southold Village - - very s ...
From $399 per night (USD)VRBO
From $254 per night (USD)VRBO
Cottage on private road and 5-min walk to beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Perfect all-season cottage with easy access to beaches, wineries, restaurants, and all the great things the North Fork h ...
From $254 per night (USD)VRBO
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Waterfront, private beach, ready for adventure, light & bright!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Set on a magical one-acre promontory, jutting into beautiful Long Creek with spectacular water views from every room, th ...
Click For PricingVRBO
From $418 per night (USD)VRBO
Bright light, water views, steps from the beach!
- Bedrooms:
- 1
- Bathrooms:
- 3
- 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 $418 per night (USD)VRBO
From $946 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 $946 per night (USD)VRBO
From $697 per night (USD)Expedia
Steps from Cedar Beach ! Tranquil Retreat in the Heart of Wine Country
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
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 $697 per night (USD)Expedia
From $774 per night (USD)VRBO
Shelter Bay Cove - North Fork Waterfront with Private Dock & Bay Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Lovingly restored with new kitchen, refinished hardwood floors throughout, two full modern bathrooms, open fireplace, ce ...
From $774 per night (USD)VRBO
From $633 per night (USD)VRBO
Private Coastal Two Bedroom Cottage on the Water
- Bedrooms:
- 1
- Bathrooms:
- 2
- 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 $633 per night (USD)VRBO
From $827 per night (USD)VRBO
Water View Beach House just steps to Private Sandy Beach!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Just steps from a private sandy beach with a beautiful view across the Peconic Bay to Sag Harbor and perfect sunsets. Ho ...
From $827 per night (USD)VRBO
From $2740 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 $2740 per night (USD)VRBO
From $1272 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 $1272 per night (USD)VRBO
From $578 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 $578 per night (USD)VRBO
From $993 per night (USD)VRBO
Luxury by the Sea
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Your search 👀 is over! Brand New 🔨 Construction. Charming, luxurious, private, comfortable Beach 🏖 House. Stunning ...
From $993 per night (USD)VRBO
From $586 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 $586 per night (USD)VRBO
From $480 per night (USD)VRBO
Lovely, Serene and Stylish Country Cottage
- 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 $480 per night (USD)VRBO
From $2190 per night (USD)VRBO
Luxury North Fork Estate w/ Heated Pool & Walk to Southold Beaches
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 12
Luxury North Fork estate in Southold with a private heated saltwater pool, spa, and walk-to-beach access. Set on over an ...
From $2190 per night (USD)VRBO
From $816 per night (USD)VRBO
Heated pool on Goose Creek, private dock, massive yard walk to beach, wineries
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Southold Permit # 0361. Pool opens Mid April! One season off of a full renovation - reviews before 2022 are from befo ...
From $816 per night (USD)VRBO
From $476 per night (USD)VRBO
Waterfront, New Construction North Fork Beach House
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Waterfront (with dock) beach house located on Goose Creek, Southold (North Fork, LI). This custom-built new construction ...
From $476 per night (USD)VRBO
From $1653 per night (USD)VRBO
5 Bedrooms ~ Steps from a Private Sandy Beach and Beautiful Vineyard Views..
- Bedrooms:
- 3
- 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 $1653 per night (USD)VRBO
From $844 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 $844 per night (USD)VRBO
From $769 per night (USD)VRBO
Southold 3BR Waterfront Home on Goose Creek | Dock, Kayaks, Single-Level
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Single-level waterfront home with three bedrooms, a private dock, and two kayaks on Goose Creek, eight minutes ...
From $769 per night (USD)VRBO
From $382 per night (USD)Expedia
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 $382 per night (USD)Expedia
From $459 per night (USD)VRBO
Southold, NY- Heart of North Fork Wine Country and Minutes From The Beach
- Bedrooms:
- 3
- 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 $459 per night (USD)VRBO
From $1490 per night (USD)VRBO
Panoramic Water Views, Plunge Pool, Hot Tub, Fire Pit & Walk to Beach
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 11
Summer comes early. Plunge Pool is open for 2026! Perfect two/three family share house as all bedrooms have en-suite bat ...
From $1490 per night (USD)VRBO
From $603 per night (USD)VRBO
Cedar-shake Cottage, Heated pool and Gardens
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Renovated three-bedroom cottage in Southold with a heated pool, awning-covered deck, and built-in grill set in ...
From $603 per night (USD)VRBO
From $4215 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 $4215 per night (USD)VRBO
From $232 per night (USD)VRBO
A Natural Getaway
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This bright house, built in 2019, is a stroll to pristine McCabe’s Sound beach and a bike ride to Southold’s lovely vill ...
From $232 per night (USD)VRBO
From $889 per night (USD)Expedia
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 $889 per night (USD)Expedia
From $651 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 $651 per night (USD)VRBO
From $576 per night (USD)VRBO
Beautiful Southold Home with a Water View - 3 Bedroom, 2.5 Bath, Sleeps 8
- Bedrooms:
- 1
- Bathrooms:
- 3
- 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 $576 per night (USD)VRBO
From $1095 per night (USD)VRBO
Perfect Waterfront Family Vacation Home next to the best vineyards in NY!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Completely renovated 3 bedroom, 2 bath Beachfront Cottage. Step outside and enjoy outdoor dining, playing games on th ...
From $1095 per night (USD)VRBO
From $822 per night (USD)VRBO
Southold Escape with Large Saltwater Pool on Wine Trail
- Bedrooms:
- 2
- 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 $822 per night (USD)VRBO
From $2278 per night (USD)VRBO
Contemporary Bayfront Retreat with NEW Heated Saltwater Pool, Bluestone...
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Vineyard Beach House Contemporary Bayfront Retreat with NEW Heated Saltwater Pool, Bluestone Patio & Private Beach Acce ...
From $2278 per night (USD)VRBO
From $1002 per night (USD)VRBO
Cozy Long Island Escape
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Enjoy all the beauty of Long Island’s North Fork with this conveniently located farmhouse. Close to wineries, farms and ...
From $1002 per night (USD)VRBO
From $522 per night (USD)VRBO
Charming Cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Charming cozy cottage located in the heart of the Northfork, East End of Long Island. Come explore the beautiful vineyar ...
From $522 per night (USD)VRBO
From $1278 per night (USD)VRBO
New Modern Farmhouse Estate Living in the heart of Southold with a pool!!!
- Bedrooms:
- 7
- Bathrooms:
- 8
- Sleeps:
- 12
Town of Southold Rental Permit Number 0816 A beautiful brand new estate home with a heated pool, situated in t ...
From $1278 per night (USD)VRBO
From $614 per night (USD)VRBO
Greenport Walk to beach & vineyard from this brand new home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Take it easy at this brand new unique retreat. Walking to distance to the beach and winery. Less than a 2 minute drive ...
From $614 per night (USD)VRBO
From $2109 per night (USD)VRBO
Modern Farmhouse Private Estate, 6.5 acres
- Bedrooms:
- 6
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to your private 6.5 acre getaway. With 4 bedrooms and 6 bathrooms, this spacious and beautifully designed home i ...
From $2109 per night (USD)VRBO
From $655 per night (USD)VRBO
4BR+ Newly renovated home mins to top beaches and vineyards, new heated pool!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
This is a newly renovated 4BR+ home in the heart of Southold with a brand new 18 x 36 heated pool and fully fenced yard. ...
From $655 per night (USD)VRBO
From $233 per night (USD)Expedia
Lake House Located Near North Fork Wineries
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This ranch house is beautifully located on a freshwater lake in the heart of Long Island's wine country, just minutes fr ...
From $233 per night (USD)Expedia
From $193 per night (USD)VRBO
Secluded Lakefront Cottage Near Town Beaches and North Fork Wineries
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This cottage is beautifully located on Great Pond on one-half acre in the heart of Long Island's North Fork. The lakefro ...
From $193 per night (USD)VRBO
From $625 per night (USD)VRBO
Sweeping Dunes Beach Cottage
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Take it easy at this unique and tranquil getaway. This newly renovated beach cottage is located on a private property on ...
From $625 per night (USD)VRBO
From $1236 per night (USD)VRBO
Newly Renovated Gem on the Cedar Beach Peninsula!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Come and experience the peaceful tranquility of the North Fork with this newly renovated gem in the heart of Southold. I ...
From $1236 per night (USD)VRBO
From $537 per night (USD)Expedia
Beautiful North Fork 3-Bedroom Home Steps Away from a Private Sandy Bay
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful vacation home in the Bay Haven community of Southold. The house is on a fully landscaped property of over a th ...
From $537 per night (USD)Expedia
From $1240 per night (USD)VRBO
Waterfront property with own dock and stunning views, overlooking Southold Bay.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to our home, a one of a kind Bayfront property with a private dock, a large, expansive deck, overlooking Southol ...
From $1240 per night (USD)VRBO
From $1366 per night (USD)Expedia
Beachfront Greenport Villa
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Stunning 3BR/2.5BA beachfront retreat in Greenport, directly on the Long Island Sound. Enjoy breathtaking water views, d ...
From $1366 per night (USD)Expedia
From $506 per night (USD)VRBO
Vine + Sand--Southold, NY'S Newest B&B Room--Room 3--Queen Bed and Ensuite Bathroom With Rain Shower
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
CHECK OUT OUR REDUCED SEASONAL RATES 6 WINERIES IN UNDER A MILE NO CLEANING FEES NO EXTRA PERSON FEES FREE BIKES FREE ...
From $506 per night (USD)VRBO
From $506 per night (USD)Expedia
Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
CHECK OUT OUR REDUCED SEASONAL RATES 6 WINERIES IN UNDER A MILE NO CLEANING FEES NO EXTRA PERSON FEES FREE BIKES FREE ...
From $506 per night (USD)Expedia
From $547 per night (USD)VRBO
Vine + Sand--Southold, NY'S Newest B&B--Room 1--King Bed and Ensuite Bathroom With Soaking Tub
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
CHECK OUT OUR REDUCED SEASONAL RATES 6 WINERIES IN UNDER A MILE NO CLEANING FEES NO EXTRA PERSON FEES FREE BIKES FREE B ...
From $547 per night (USD)VRBO
From $1011 per night (USD)VRBO
North Fork Waterfront Gem!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Live the waterfront life! Kayak, paddle board, boat from your front door! Enjoy gathering your own oysters and clams fro ...
From $1011 per night (USD)VRBO
From $1444 per night (USD)VRBO
A cozy and family-friendly haven with heated pool, minutes from the beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 13
A family-friendly home that covers all the bases. Everything your family needs (toys, cribs, bouncers, tub, playmats, hi ...
From $1444 per night (USD)VRBO
From $397 per night (USD)VRBO
Lovely 4 Bedroom Southold Home Walking Distance to Peconic Bay
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 6
Beautiful and quiet corner home in a lovely neighborhood in Southold. 100 year old farmhouse but with modern convenienc ...
From $397 per night (USD)VRBO
From $562 per night (USD)VRBO
Newly Constructed Modern Vacation Villa Minutes to some of the best...
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Villa Vino Modern Newly Constructed Modern Vacation Villa Minutes to some of the best wineries on the North Fork, Perfe ...
From $562 per night (USD)VRBO
From $976 per night (USD)Expedia
Perfect Retreat for Families - Close to Amazing Wineries, Beaches, and Dining!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Enjoy the NOFO life - full of farm to table food, amazing oysters, and beaches! This newly renovated stylish house sle ...
From $976 per night (USD)Expedia
From $616 per night (USD)VRBO
Updated Historic shingle-style 1902 4-bedroom Beach House on Southold Bay!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
You are invited to have a wonderful time in this Southold, Long Island beach house. You will have a fabulous time of sun ...
From $616 per night (USD)VRBO
From $516 per night (USD)VRBO
Southold retreat-- Indoor/outdoor living near immaculate beaches & wineries
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your perfect summer getaway located in the desirable Claves Neck neighborhood, minutes from northfork's great ...
From $516 per night (USD)VRBO
From $606 per night (USD)VRBO
Charming North Fork Beach Cottage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our Peconic home, our home away from home. We invite you to stay in our air conditioned home in the quaint ha ...
From $606 per night (USD)VRBO
From $2609 per night (USD)VRBO
Luxury north fork estate
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Absolutely stunning custom home Italian Tuscan style villa on the outside. Modern Hamptons vibe on the inside . 1 acre + ...
From $2609 per night (USD)VRBO
From $918 per night (USD)VRBO
NORTH FORK DREAM HOME, 4,000 Sq Ft, 1 Acre, Heated Pool!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Make yourself at home in this spacious and beautiful North Fork Wine Country home in the heart of Southold! This 4,000 s ...
From $918 per night (USD)VRBO
From $1110 per night (USD)VRBO
Stylish beach getaway: pool in prime location
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our beautifully renovated, designer-decorated home in the heart of Southold, NY! Perfectly located within wal ...
From $1110 per night (USD)VRBO
From $811 per night (USD)VRBO
“Paradise Found” - Walk to Private Beach & In-Ground Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to paradise with this stunning north fork home, where relaxation and adventure meet! A quick walk to the beach, t ...
From $811 per night (USD)VRBO
From $558 per night (USD)VRBO
Family Beach House on the North Fork of Long Island
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to our Family Beach House, nestled on the coast of the Peconic Bay in the charming town of Southold, New York. E ...
From $558 per night (USD)VRBO
From $2479 per night (USD)VRBO
Spacious Home with Pool in Southold
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Discover this sun-filled 4-bedroom Southold home, perfect for a relaxing escape. Enjoy a luxurious saltwater pool, cozy ...
From $2479 per night (USD)VRBO
From $581 per night (USD)Expedia
Charming waterfront, 3-bedroom house on Goose Creek in welcoming Southold
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy a peaceful stay at this delightful 3-bedroom house on a park like, waterfront property in Southold. With a hot tub ...
From $581 per night (USD)Expedia
From $494 per night (USD)VRBO
Adorable Cottage Home - Charming 2-bedroom house in delightful Southold
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Unwind in Southold at this lovely house. This tranquil retreat features 2 bedrooms, including a king bed and 2 twin beds ...
From $494 per night (USD)VRBO
From $1203 per night (USD)Expedia
Country BEACH home!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Perfection!! Amazing, centrally 🌊 located getaway in the middle of EVERYTHING that the North🍷Fork has to offer. BEAUT ...
From $1203 per night (USD)Expedia
From $550 per night (USD)VRBO
Expansive North Fork Estate on almost 3 Acres, Close to Vineyards and...
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Please note that a reservation for this property needs to be approved before it is confirmed. North Fork Farmhouse Exp ...
From $550 per night (USD)VRBO
From $1165 per night (USD)Expedia
North Fork Summer Escape - 5BR Waterfront Home with Private Beach Access
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to our spacious 5-bedroom waterfront retreat in Southold, North Fork, Long Island. Just steps from a private san ...
From $1165 per night (USD)Expedia
From $809 per night (USD)VRBO
Waterfront Hot Tub Retreat w Kayaks | Kayak Point
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Kayak Point is a private waterfront home on Southold’s Long Creek, featuring a hot tub with water views, kayak ...
From $809 per night (USD)VRBO
From $1824 per night (USD)VRBO
Sunset Perch, Modern Southold Home with Rooftop Deck and Heated Pool
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Summary: Sunset Perch is a modern home set across four levels on Southold’s North Fork, a 5-minute walk from Southold T ...
From $1824 per night (USD)VRBO
From $1154 per night (USD)VRBO
Newly Renovated, Stylish Peconic Retreat with Private Pool, Lush Grounds,...
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
North Fork Chic Newly Renovated, Stylish Peconic Retreat with Private Pool, Lush Grounds, Perfect for Families. 4BR/2. ...
From $1154 per night (USD)VRBO
From $794 per night (USD)Expedia
Spacious Vacation 4BR Home Near Southold Beach, Greenport, and Top Wineries
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy a relaxing North Fork getaway in this spacious vacation rental, ideally located just minutes from Southold Town Be ...
From $794 per night (USD)Expedia
From $493 per night (USD)VRBO
Surrounded by nature, come stay in this serene location
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Perfect for a relaxing getaway. Book now and enjoy everything this house has to offer. **** This is an apartment with ...
From $493 per night (USD)VRBO
From $1476 per night (USD)VRBO
Modern Waterfront Southold Escape, Private Heated Saltwater Pool, Great for...
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Please note that a reservation for this property needs to be approved before it is confirmed. The Waterside Hideaway M ...
From $1476 per night (USD)VRBO
From $442 per night (USD)VRBO
Southold Waterfront Home on Goose Creek | Dock, Kayaks, Creek Views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Waterfront home on Goose Creek with a private dock and kayaks for direct water access. Three bedrooms and thre ...
From $442 per night (USD)VRBO
From $905 per night (USD)VRBO
Nautical Peconic Bayfront Home - Walk to Town
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Gorgeous, renovated 4 bedroom waterfront home in prime Southold. Enjoy an outdoor fire next to the bay, or cozy up next ...
From $905 per night (USD)VRBO
From $721 per night (USD)VRBO
Traditional Southold Home, Private Heated Saltwater Pool, Perfect for Families
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Please note that a reservation for this property needs to be approved before it is confirmed. The Southold Retreat Tra ...
From $721 per night (USD)VRBO
From $1168 per night (USD)VRBO
Waterfront swim access Newly built 4BR/3BA sleep 8 Dedicated workspace fast WiFi
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Wake up on the water. This newly built four-bedroom sits directly on the water on Southold’s most desired waterway, with ...
From $1168 per night (USD)VRBO
From $554 per night (USD)VRBO
North Fork Escape: Near Bay Beaches, Farms & Wine Country
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Southold awaits at this cozy 3-bedroom high ranch. Inside, the main floor offers 3 bedrooms, 2 bathrooms, kitchen, livin ...
From $554 per night (USD)VRBO
From $1268 per night (USD)Expedia
Founders Landing, Salt Water Heated Pool, Walk To Beach, Town, Restaurants
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Welcome to our home. We are located in the historic Founders Landing community of Southold, up the block from the pristi ...
From $1268 per night (USD)Expedia
From $386 per night (USD)VRBO
North Fork Wine Country Bungalow
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Huge one bedroom bungalow with water views. Walking distance to private beach and a winery The Space: Thi ...
From $386 per night (USD)VRBO
From $1427 per night (USD)Expedia
Steps from Surf and Sand in Southold!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Fourteen day rental requirement per local laws with substantial discounts available for light use and/or extended stay. ...
From $1427 per night (USD)Expedia
From $805 per night (USD)VRBO
Enjoy Driftwood Landing - A Quiet Southold Escape
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Driftwood Landing has been our family vacation home for years and we hope you enjoy it here as much as we do! We find it ...
From $805 per night (USD)VRBO
From $469 per night (USD)Expedia
Cedar Point Cove - Waterfront Escape with Private Dock and Peconic Bay Views
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Cedar Point Cove sits right on the water in one of Southold's most sought-after waterfront communities on the North Fork ...
From $469 per night (USD)Expedia
From $725 per night (USD)VRBO
Heaven Off Main
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Heaven Off Main, a thoughtfully designed retreat in Southold, NY, nestled in the heart of Long Island’s North ...
From $725 per night (USD)VRBO
From $558 per night (USD)VRBO
Modern Glass House, Heated Lap Pool, Private Southold Woods
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: A modern, glass-walled home on a private wooded lot in Southold, with a heated lap pool, mid-century interiors ...
From $558 per night (USD)VRBO