Southold, New York Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Southold, New York on RentalSaver.com!

Southold Rentals

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VRBO
The perfect north fork experience
Bedrooms:
4
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 ...
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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
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VRBO
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 ...
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VRBO
From $839 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 $839 per night (USD)
Expedia
From $709 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 $709 per night (USD)
VRBO
From $1437 per night (USD)
VRBO
4 Bed / 2.5 Bath Stunning North Fork retreat with Heated Pool & Hot Tub
Bedrooms:
1
Bathrooms:
4
Sleeps:
10
Our home sits on 3+ acres. The Great Room has a stone fireplace and magnificent vaulted ceilings. Sliding doors lead dir ...
From $1437 per night (USD)
VRBO
From $557 per night (USD)
VRBO
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 $557 per night (USD)
VRBO
From $330 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 $330 per night (USD)
Expedia
From $236 per night (USD)
VRBO
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 $236 per night (USD)
VRBO
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Expedia
Private Beach community home nestled in the heart of Long Island's North Fork
Bedrooms:
2
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 ...
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Expedia
From $628 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 $628 per night (USD)
VRBO
From $604 per night (USD)
Expedia
Steves Place Heated Pool, 3BR Southold Home
Bedrooms:
1
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 $604 per night (USD)
Expedia
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VRBO
A Natural Getaway
Bedrooms:
2
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 ...
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VRBO
From $445 per night (USD)
Expedia
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 $445 per night (USD)
Expedia
From $748 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 $748 per night (USD)
VRBO
From $490 per night (USD)
Expedia
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 $490 per night (USD)
Expedia
From $490 per night (USD)
VRBO
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 $490 per night (USD)
VRBO
From $538 per night (USD)
Expedia
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 $538 per night (USD)
Expedia
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Expedia
Cozy North Fork Home with Direct Water Access, Private Dock, Close to Wineries
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Waterfront Chic Cozy North Fork Home with Direct Water Access, Private Dock, Close to Wineries 4BR/3BA: private pool, ...
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Expedia
From $1734 per night (USD)
Expedia
Beautiful waterfront home with pool, hot tub dock kayaks bocce etc Sleeps 10
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Amidst north fork wineries steps from sandy beach. Private dock, kayaks, paddle board, private community. Spacious 5 b ...
From $1734 per night (USD)
Expedia
From $906 per night (USD)
VRBO
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 $906 per night (USD)
VRBO
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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 ...
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VRBO
$Southold retreat-- Indoor/outdoor living near immaculate beaches & wineries\n\n\n\n$
From $477 per night (USD)
VRBO
Southold retreat-- Indoor/outdoor living near immaculate beaches & wineries\n\n\n\n
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 $477 per night (USD)
VRBO
From $569 per night (USD)
Expedia
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 $569 per night (USD)
Expedia
From $3381 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 $3381 per night (USD)
VRBO
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Expedia
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 ...
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Expedia
From $979 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 $979 per night (USD)
VRBO
From $828 per night (USD)
Expedia
“Paradise Found” - Walk to Private Beach & In-Ground Pool!
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Escape to paradise with this stunning north fork home, where relaxation and adventure meet! A quick walk to the beach, t ...
From $828 per night (USD)
Expedia
From $614 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 $614 per night (USD)
VRBO
From $1138 per night (USD)
VRBO
Discover the Perfect Northfork Home
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Discover the best of Southold in this sophisticated 4-bedroom, 3.5-bath home, ideally situated close to Town Beach & K ...
From $1138 per night (USD)
VRBO
From $1285 per night (USD)
VRBO
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 $1285 per night (USD)
VRBO
From $619 per night (USD)
Expedia
Expansive North Fork Estate on almost 3 Acres, Close to Vineyards and...
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
North Fork Farmhouse Expansive North Fork Estate on almost 3 Acres, Close to Vineyards and Beaches, Perfect for Familie ...
From $619 per night (USD)
Expedia
From $645 per night (USD)
VRBO
Cozy North Fork Home with Direct Water Access, Private Dock, Close to Wineries
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Please note that a reservation for this property needs to be approved before it is confirmed. Waterfront Chic Cozy Nor ...
From $645 per night (USD)
VRBO
From $1004 per night (USD)
Expedia
Peconic Bay Beach House + 5 bedrooms + spacious +
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 $1004 per night (USD)
Expedia
From $1174 per night (USD)
VRBO
Beautifully farmhouse
Bedrooms:
3
Bathrooms:
5
Sleeps:
7
<p>A short distance from ice skating, sailing, and more, this family-friendly vacation home lets you experience it all. ...
From $1174 per night (USD)
VRBO
From $372 per night (USD)
VRBO
Charming 2-bedroom home with AC in the heart of Wine Country
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Stay comfortably in Southold at this 2-bedroom home. This gorgeous property features 1 queen bed and one full over queen ...
From $372 per night (USD)
VRBO
From $784 per night (USD)
VRBO
Serene Southold Beach Bliss, heated saltwater pool, family-friendly
Bedrooms:
4
Bathrooms:
3
Sleeps:
10
Welcome to our sun-filled Southold getaway on the North Fork of Long Island. Newly available for the 2025 rental season, ...
From $784 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:
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 $468 per night (USD)
VRBO
From $766 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 $766 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 $552 per night (USD)
VRBO
Located in the heart of wine country/BEACHES/shops.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Historical home full of charm. A home built in the 1700's this home maintains the historical feel with all the amenitie ...
From $552 per night (USD)
VRBO
From $2964 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 $2964 per night (USD)
VRBO
From $531 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 $531 per night (USD)
VRBO
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 $769 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 $769 per night (USD)
VRBO
From $2371 per night (USD)
VRBO
Panoramic Water Views, Plunge Pool, Hot Tub, Fire Pit & Walk to Beach
Bedrooms:
4
Bathrooms:
4
Sleeps:
11
Returning Guests - new additions in 2025: Soake plunge pool, additional sleep space within office, new landscape across ...
From $2371 per night (USD)
VRBO
From $591 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 $591 per night (USD)
VRBO
From $485 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 $485 per night (USD)
VRBO
From $1652 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 $1652 per night (USD)
VRBO
From $787 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 $787 per night (USD)
VRBO
From $524 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 $524 per night (USD)
VRBO
From $495 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 $495 per night (USD)
VRBO
From $1653 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 $1653 per night (USD)
VRBO
From $334 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 $334 per night (USD)
VRBO
From $2241 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 $2241 per night (USD)
VRBO
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
From $1001 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 $1001 per night (USD)
VRBO
From $543 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 $543 per night (USD)
VRBO
From $227 per night (USD)
VRBO
Sweet Southold Beach Cottage FALL WINTER SPRING SUMMER 1 min walk to beach
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 $227 per night (USD)
VRBO
From $937 per night (USD)
Expedia
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 $937 per night (USD)
Expedia
From $779 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 both ...
From $779 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 $585 per night (USD)
VRBO
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 ...
From $585 per night (USD)
VRBO
From $367 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 $367 per night (USD)
VRBO
From $981 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 $981 per night (USD)
VRBO
From $658 per night (USD)
Expedia
Shelter Bay Cove Waterfront + Beach + spectacular
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Lovingly restored with new kitchen, refinished hardwood floors throughout, two full modern bathrooms, open fireplace, ce ...
From $658 per night (USD)
Expedia
From $548 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 $548 per night (USD)
VRBO
From $312 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 $312 per night (USD)
VRBO
From $993 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 $993 per night (USD)
VRBO
From $518 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 $518 per night (USD)
VRBO
From $414 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 $414 per night (USD)
VRBO
From $383 per night (USD)
Expedia
Architect-Renovated, Pristine Ranch, Modern Kitchen, Short Walk to Beach
Bedrooms:
2
Bathrooms:
2
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)
Expedia
From $879 per night (USD)
VRBO
Beautiful updated home with pool by Wineries and Beaches - “The Vacation House”
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Farmhouse meets beach house at “The Vacation House”…beautiful North Fork Farm House in relaxing farm/beach area perfect ...
From $879 per night (USD)
VRBO
From $1200 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 $1200 per night (USD)
Expedia
From $543 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 $543 per night (USD)
VRBO
From $1050 per night (USD)
VRBO
Beachfront - endless sunsets, sandy beach, cozy sunroom & open concept kitchen
Bedrooms:
2
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 $1050 per night (USD)
VRBO
From $1088 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 $1088 per night (USD)
VRBO
Click For Pricing
Expedia
Southold near vineyard & beach
Bedrooms:
0
Bathrooms:
0
Sleeps:
0
Enjoy a stylish experience at this centrally-located historic charmer. Have cocktails on the balcony, cook in the fully ...
Click For Pricing
Expedia
From $1142 per night (USD)
VRBO
North Fork 7 Bedroom Farmhouse Escape
Bedrooms:
3
Bathrooms:
7
Sleeps:
10
Enjoy this comfortable farmhouse with seven bedrooms, living room, full formal dinning room for 10, eat in kitchen, wrap ...
From $1142 per night (USD)
VRBO
$Charming Farmhouse with Pool and Large Yard \nCentrally Located and Walkable$
From $863 per night (USD)
VRBO
Charming Farmhouse with Pool and Large Yard \nCentrally Located and Walkable
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Walking distance from the Jitney, LIRR & Southold Village. Deck, massive barbecue, indoor soaking tub & outdoor shower. ...
From $863 per night (USD)
VRBO
From $525 per night (USD)
VRBO
Newly Constructed Modern Vacation Villa Minutes to some of the best...
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Please note that a reservation for this property needs to be approved before it is confirmed. Villa Vino Modern Newly ...
From $525 per night (USD)
VRBO
From $291 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 $291 per night (USD)
Expedia
From $1866 per night (USD)
VRBO
Resort-Style Southold Retreat with Private Pool, Guest House, and Chic...
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Please note that a reservation for this property needs to be approved before it is confirmed. The Southold Escape Reso ...
From $1866 per night (USD)
VRBO
From $374 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 $374 per night (USD)
VRBO
From $855 per night (USD)
VRBO
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 $855 per night (USD)
VRBO
From $1616 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 $1616 per night (USD)
VRBO
From $760 per night (USD)
VRBO
Kayak Point: Waterfront, Hot Tub, Viewing Deck
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: Discover a tranquil waterfront haven on Southold's Long Creek and Hashamomuck Pond. Nestled among tall oaks on ...
From $760 per night (USD)
VRBO
From $966 per night (USD)
VRBO
Charming Southold Waterfront Property
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Welcome to our beautiful waterfront home with breathtaking views of Hashamomuck Pond—an idyllic setting for an unforgett ...
From $966 per night (USD)
VRBO
From $244 per night (USD)
VRBO
Cozy studio with WiFi and AC in welcoming Southold
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Nestled in Southold, this delightful studio offers a superb stay for guests. Attached to our main house, this private st ...
From $244 per night (USD)
VRBO
From $1544 per night (USD)
VRBO
Sunset Perch: Private Pool, Rooftop Deck
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Summary: Experience elevated coastal living in this contemporary and light-filled North Fork retreat set on a private la ...
From $1544 per night (USD)
VRBO
From $227 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 $227 per night (USD)
VRBO
From $914 per night (USD)
VRBO
Serenity on the North Fork
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Mediterranean style newly renovated home on a private waterfront property. Enjoy beautiful sunsets and views of the Lon ...
From $914 per night (USD)
VRBO
From $382 per night (USD)
VRBO
North Fork Retreat
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Keep it simple at this peaceful and centrally-located light filled north fork cottage. Creek views with large yard and m ...
From $382 per night (USD)
VRBO
From $661 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 $661 per night (USD)
VRBO
From $2696 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 $2696 per night (USD)
VRBO
From $470 per night (USD)
VRBO
SPRING DISCOUNT - COTTAGE ON LONG ISLAND SOUND, PRIVATE BEACH, GLORIOUS SUNSETS
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
This charming cedar shingled beach cottage is located steps away from Long Island Sound with stairs leading down to its ...
From $470 per night (USD)
VRBO
From $614 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 $614 per night (USD)
VRBO
From $1405 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 $1405 per night (USD)
VRBO
Click For Pricing
VRBO
Beautiful private home with beach access down the block
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
1/2 acre fenced property. open floor plan. Master with en suite bathroom. additional bedrooms and bathrooms for your use ...
Click For Pricing
VRBO
From $1024 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 $1024 per night (USD)
VRBO

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Results: 183 Rentals