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

Southold Rentals

From $610 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 $610 per night (USD)
VRBO
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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 ...
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Expedia
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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 $745 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 $745 per night (USD)
VRBO
From $1600 per night (USD)
VRBO
Charming English Tudor
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
This spacious and charming 4,500 square foot English Tudor is situated on 2.25 acres in Southold. It has 4 bedrooms, 3 b ...
From $1600 per night (USD)
VRBO
From $2063 per night (USD)
Expedia
Exquisite Private Retreat
Bedrooms:
5
Bathrooms:
5
Sleeps:
18
Custom chic private retreat on 2.5 acres in Southold. Enjoy the best of every season in this artfully designed top to b ...
From $2063 per night (USD)
Expedia
From $485 per night (USD)
VRBO
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 $485 per night (USD)
VRBO
From $512 per night (USD)
Expedia
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 $512 per night (USD)
Expedia
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VRBO
Goose Creek Getaway: Modern Home with Beach Access
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Goose Creek Getaway is a beautifully remodeled 3-bedroom, 2 full baths North Fork vacation home just a 1-minute drive in ...
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VRBO
$4 Bed \/ 2.5 Bath Stunning North Fork retreat with Heated Pool & Hot Tub$
From $1218 per night (USD)
VRBO
4 Bed \/ 2.5 Bath Stunning North Fork retreat with Heated Pool & Hot Tub
Bedrooms:
3
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 $1218 per night (USD)
VRBO
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VRBO
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 ...
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VRBO
From $534 per night (USD)
Expedia
Private Waterfront Home: Dock, Kayaks, Town of Southold, near Greenport
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Private Waterfront Home is a beautiful home located on the North Fork of Long Island, it has a Master bedroom with a qu ...
From $534 per night (USD)
Expedia
From $261 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 $261 per night (USD)
VRBO
From $221 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 $221 per night (USD)
Expedia
From $500 per night (USD)
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 ...
From $500 per night (USD)
VRBO
From $614 per night (USD)
Expedia
Spacious Waterfront Home with Outstanding Waterviews!
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Fabulous four bedroom waterfront home located on a private road on Hashamomuck Pond. Sit back, relax in the backyard an ...
From $614 per night (USD)
Expedia
From $625 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 $625 per night (USD)
VRBO
From $690 per night (USD)
Expedia
Steve's Place: Heated Pool, 3BR Southold Home, Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Steve's Place is a beautifully and professionally decorated 3-bedroom with 1.5 bathrooms, North fork vacation home is ju ...
From $690 per night (USD)
Expedia
From $389 per night (USD)
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 ...
From $389 per night (USD)
VRBO
From $478 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 $478 per night (USD)
Expedia
From $688 per night (USD)
VRBO
Greenport Walk to beach & vineyard from this brand new home
Bedrooms:
3
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 $688 per night (USD)
VRBO
$5 bed, 4.5 bath home on 1.24 acres w\/ pool$
From $1251 per night (USD)
VRBO
5 bed, 4.5 bath home on 1.24 acres w\/ pool
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Perfect summer getaway with 5 bed, 4.5 bath in the heart of the North Fork. The home sits on 1.24 acres and features an ...
From $1251 per night (USD)
VRBO
From $780 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 $780 per night (USD)
VRBO
From $370 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 $370 per night (USD)
Expedia
From $374 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 $374 per night (USD)
VRBO
From $406 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 $406 per night (USD)
Expedia
From $1518 per night (USD)
VRBO
Beautiful waterfront home with pool, hot tub dock kayaks bocce etc Sleeps 10
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Amidst north fork wineries steps from sandy beach. Private dock, kayaks, paddle board, private community. Spacious 5 b ...
From $1518 per night (USD)
VRBO
From $903 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 $903 per night (USD)
Expedia
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VRBO
Updated Historic shingle-style 1902 4-bedroom Beach House on Southold Bay!
Bedrooms:
5
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 $412 per night (USD)
Expedia
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 $412 per night (USD)
Expedia
From $505 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 $505 per night (USD)
VRBO
From $3067 per night (USD)
Expedia
Luxury north fork estate
Bedrooms:
5
Bathrooms:
3
Sleeps:
6
Absolutely stunning custom home Italian Tuscan style villa on the outside. Modern Hamptons vibe on the inside . 1 acre + ...
From $3067 per night (USD)
Expedia
From $1080 per night (USD)
VRBO
NORTH FORK DREAM HOME, 4,000 Sq Ft, 1 Acre, Heated Pool!
Bedrooms:
4
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 $1080 per night (USD)
VRBO
From $857 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 $857 per night (USD)
VRBO
From $272 per night (USD)
VRBO
Waterfront Southold Retreat < 3 Mi to Wineries!
Bedrooms:
3
Bathrooms:
6
Sleeps:
8
Escape to 'Kayak Point' and experience the beauty of Long Island's North Fork! This 4-bedroom, 2.5-bath home in Southold ...
From $272 per night (USD)
VRBO
From $500 per night (USD)
Expedia
North Fork Dream Getaway, Walk to Private Beach & New In-Ground Pool!
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Discover this fabulous 3-bedroom gem in Southold. This house features 1 king bed & 4 twin beds, perfect for a comfortabl ...
From $500 per night (USD)
Expedia
From $399 per night (USD)
VRBO
Beach House on the North Fork of Long Island
Bedrooms:
3
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 $399 per night (USD)
VRBO
$Discover the Perfect Northfork Home\n$
From $809 per night (USD)
VRBO
Discover the Perfect Northfork Home\n
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 $809 per night (USD)
VRBO
From $493 per night (USD)
VRBO
Charming 3-bedroom house with on Goose Creek in welcoming Southold
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Enjoy a peaceful stay at this delightful 3-bedroom house in Southold. With amenities like gourmet kitchen, AC, WiFi, chi ...
From $493 per night (USD)
VRBO
$Hamptons Style\/North Fork Chill and Grill. 1 mile to beaches. Onsite manager.$
From $542 per night (USD)
VRBO
Hamptons Style\/North Fork Chill and Grill. 1 mile to beaches. Onsite manager.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Quiet neighborhood 1 mile from Sound and Bay. Private huge pool (closes October 7) and deck. Grill on upper deck off of ...
From $542 per night (USD)
VRBO
From $1096 per night (USD)
VRBO
Charming North Fork farmhouse In the heart of wine country
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Unwind in Southold at this secluded farmhouse. Newly updated to include 4 bedrooms - 2 king beds, 1 queen bed, and 2 tw ...
From $1096 per night (USD)
VRBO
From $740 per night (USD)
VRBO
Amazing North Fork Townhouse Prime A+ Location Vineyards Beach Breweries Peace
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
The heart of Southold offers this new to the market luxury light filled end unit townhouse tucked away in a friendly com ...
From $740 per night (USD)
VRBO
From $538 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 $538 per night (USD)
VRBO
From $316 per night (USD)
VRBO
North fork Private exclusive Residence for Rent
Bedrooms:
3
Bathrooms:
6
Sleeps:
8
Spacious 3 bedroom ...3 1/2 bathroom modern house with large swimming pool .close to the beach and vine yards. Large ea ...
From $316 per night (USD)
VRBO
From $2164 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 $2164 per night (USD)
VRBO
From $491 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 $491 per night (USD)
VRBO
$Beach Front in Southold; newly renovated\/baths\/kitchen\/2nd floor family room!$
From $858 per night (USD)
VRBO
Beach Front in Southold; newly renovated\/baths\/kitchen\/2nd floor family room!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Newly renovated with two full bathrooms, kitchen and second floor entertainment/family/ bedroom with glorious views over ...
From $858 per night (USD)
VRBO
From $396 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 $396 per night (USD)
VRBO
$Located in the heart of wine country\/BEACHES\/shops.$
From $483 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 $483 per night (USD)
VRBO
From $702 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 $702 per night (USD)
VRBO
From $727 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 $727 per night (USD)
VRBO
From $1703 per night (USD)
VRBO
Panoramic Water Views, hot tub, fire pit & easy access to North Fork wine trail
Bedrooms:
5
Bathrooms:
5
Sleeps:
11
All bedrooms have en-suite bathrooms! On the main floor you will find a living room with electric fireplace, modern kit ...
From $1703 per night (USD)
VRBO
From $537 per night (USD)
VRBO
3 minute walk from a private beach!
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Renovated 4 BR 2 Bath home located on a private street with private beach down the road. 3 Bedrooms on the 2nd floor al ...
From $537 per night (USD)
VRBO
From $1540 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 $1540 per night (USD)
VRBO
From $342 per night (USD)
VRBO
Salt & Sea House - beaches, wineries, farms nearby
Bedrooms:
3
Bathrooms:
3
Sleeps:
11
Close to beaches, wineries, farms, and restaurants--the Salt and Sea House is a relaxing North Fork getaway. Uncork a b ...
From $342 per night (USD)
VRBO
From $383 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 $383 per night (USD)
VRBO
From $1392 per night (USD)
VRBO
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 $1392 per night (USD)
VRBO
From $684 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 $684 per night (USD)
VRBO
From $983 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 $983 per night (USD)
VRBO
From $471 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 $471 per night (USD)
VRBO
From $385 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 $385 per night (USD)
VRBO
From $442 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 $442 per night (USD)
VRBO
From $459 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 $459 per night (USD)
VRBO
From $1395 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 $1395 per night (USD)
VRBO
From $612 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 $612 per night (USD)
VRBO
$Lovely home w\/ water views, steps to beach!$
From $485 per night (USD)
VRBO
Lovely home w\/ water views, steps to 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 $485 per night (USD)
VRBO
From $889 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 $889 per night (USD)
VRBO
From $552 per night (USD)
VRBO
Shelter Bay Cove Waterfront, North Fork , Hamptons ,Long Island
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
World class views of water and sunsets are the signature features of this charming, 3 bedroom house with 90 feet of wate ...
From $552 per night (USD)
VRBO
From $380 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 $380 per night (USD)
VRBO
Click For Pricing
Expedia
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 ...
Click For Pricing
Expedia
From $729 per night (USD)
VRBO
Beautiful Home with Pool by Wineries and Beaches - “The Vacation House”
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
Farmhouse meets beach house at “The Vacation House”…beautiful North Fork Farm House in relaxing farm/beach area perfect ...
From $729 per night (USD)
VRBO
From $855 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 $855 per night (USD)
Expedia
From $612 per night (USD)
VRBO
90 feet of private waterfront w beach, new renovation, panoramic views
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Spacious and Luxurious 3 bedroom; brand new construction with 120 feet of waterfront and spectacular sunset views • 2 l ...
From $612 per night (USD)
VRBO
$Privacy!! Heated salt-water pool, central a\/c, all kinds of families welcome$
From $850 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 $850 per night (USD)
VRBO
From $342 per night (USD)
VRBO
Southold cottage with Private Beach Rights ~ Walk to Kayak & Paddle Board
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
What a cutie pie! This adorable cottage is in one of Southold's most beautiful neighborhoods. If you like to kayak or pa ...
From $342 per night (USD)
VRBO
From $192 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 $192 per night (USD)
VRBO
From $670 per night (USD)
VRBO
Walk to Sandy Beach & Town! Heated Saltwater Pool. Scroll to bottom CONTACT HOST
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
5 bedroom, classically styled home in the quiet and charming Founders Landing community. Splash around in the 20x40 in ...
From $670 per night (USD)
VRBO
From $207 per night (USD)
VRBO
RENOVATED SOUTHOLD BEACH COTTAGE - Walk to beach, restaurants, Jitney, LIRR
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
BEAUTIFUL North Fork Just renovated cottage in Founders Landing Beach Community in Historic Southold Village. ideal for ...
From $207 per night (USD)
VRBO
From $540 per night (USD)
VRBO
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 $540 per night (USD)
VRBO
From $302 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 $302 per night (USD)
VRBO
From $270 per night (USD)
VRBO
Quaint Cottage Close to LI Sound
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
This newly renovated cottage is located in the middle of wine country and close to the Long Island Sound. The property i ...
From $270 per night (USD)
VRBO
From $646 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 $646 per night (USD)
VRBO
From $486 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 $486 per night (USD)
VRBO
From $393 per night (USD)
VRBO
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 $393 per night (USD)
VRBO
From $1592 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 $1592 per night (USD)
VRBO
From $1108 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 $1108 per night (USD)
Expedia
From $445 per night (USD)
VRBO
Southold McCabe's Beach Retreat - Walk to the beach; Relax & enjoy all seasons!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Carefree retreat by the beach: recently renovated, wonderfully furnished. CAC, 3 large bedrooms, 2 full baths, open conc ...
From $445 per night (USD)
VRBO
From $980 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 $980 per night (USD)
VRBO
From $1000 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 $1000 per night (USD)
VRBO
From $493 per night (USD)
Expedia
Sprawling waterfront home with bikes, kayaks, pool table, and grill - dogs ok
Bedrooms:
4
Bathrooms:
5
Sleeps:
2
The North Fork Beach House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply en ...
From $493 per night (USD)
Expedia
Click For Pricing
VRBO
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
VRBO
From $1110 per night (USD)
Expedia
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 $1110 per night (USD)
Expedia
$Eat, Love, Stay, Swim Southold North Fork\nCentrally Located and Walkable$
From $370 per night (USD)
VRBO
Eat, Love, Stay, Swim Southold North Fork\nCentrally Located and Walkable
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Walking distance from Jitney, LIRR & Southold village. Deck, massive barbecue, indoor soaking tub & outdoor shower. Salt ...
From $370 per night (USD)
VRBO
From $1800 per night (USD)
VRBO
Spacious Home with Pool in Southold
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Discover this sun-filled 4-bedroom Southold home, perfect for a relaxing escape. Enjoy a luxurious saltwater pool, cozy ...
From $1800 per night (USD)
VRBO
From $585 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 $585 per night (USD)
VRBO
From $265 per night (USD)
Expedia
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 $265 per night (USD)
Expedia
From $384 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 $384 per night (USD)
VRBO
From $840 per night (USD)
VRBO
Serenity on the North Fork
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Mediterranean style newly renovated home on a private waterfront property. Enjoy beautiful sunsets and views of the Lon ...
From $840 per night (USD)
VRBO
From $285 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 $285 per night (USD)
VRBO
From $670 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 $670 per night (USD)
VRBO

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Results: 192 Rentals