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 $738 per night (USD)
Expedia
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 $738 per night (USD)
Expedia
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 $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 $624 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 $624 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
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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 $212 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 $212 per night (USD)
Expedia
From $667 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 $667 per night (USD)
VRBO
From $320 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 $320 per night (USD)
Expedia
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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 ...
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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 $530 per night (USD)
Expedia
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 $530 per night (USD)
Expedia
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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 ...
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VRBO
From $444 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 $444 per night (USD)
Expedia
From $706 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 $706 per night (USD)
VRBO
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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 $545 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 $545 per night (USD)
VRBO
From $513 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 $513 per night (USD)
Expedia
From $546 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 $546 per night (USD)
VRBO
From $1518 per night (USD)
Expedia
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)
Expedia
From $861 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 $861 per night (USD)
VRBO
From $680 per night (USD)
Expedia
Updated Historic shingle-style 1902 4-bedroom Beach House on Southold Bay!
Bedrooms:
4
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 $680 per night (USD)
Expedia
$Southold retreat-- Indoor\/outdoor living near immaculate beaches & wineries\n\n\n\n$
From $436 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 $436 per night (USD)
VRBO
From $505 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 $505 per night (USD)
Expedia
From $3057 per night (USD)
VRBO
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 $3057 per night (USD)
VRBO
From $1477 per night (USD)
Expedia
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 $1477 per night (USD)
Expedia
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
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Expedia
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 ...
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Expedia
From $593 per night (USD)
VRBO
North Fork Dream Getaway, 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 $593 per night (USD)
VRBO
From $399 per night (USD)
Expedia
Family 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)
Expedia
From $982 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 $982 per night (USD)
VRBO
From $783 per night (USD)
Expedia
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 $783 per night (USD)
Expedia
From $1317 per night (USD)
VRBO
Expansive North Fork Estate on almost 3 Acres, Close to Vineyards and...
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
North Fork Farmhouse Expansive North Fork Estate on almost 3 Acres, Close to Vineyards and Beaches, Perfect for Familie ...
From $1317 per night (USD)
VRBO
From $999 per night (USD)
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, ...
From $999 per night (USD)
Expedia
From $897 per night (USD)
VRBO
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 $897 per night (USD)
VRBO
From $795 per night (USD)
Expedia
Magic Place
Bedrooms:
3
Bathrooms:
5
Sleeps:
7
<p>Located in Southold, this welcoming vacation home lets you experience it all. With the property's convenient onsite p ...
From $795 per night (USD)
Expedia
From $504 per night (USD)
VRBO
Waterfront Beach House Nestled Along the Wondrous North Fork Wine Trail,...
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Please note that a reservation for this property needs to be approved before it is confirmed. Wine Trail Waterfront Wa ...
From $504 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 $807 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 $807 per night (USD)
Expedia
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 $2668 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 $2668 per night (USD)
VRBO
From $495 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 $495 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 $2323 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 $2323 per night (USD)
VRBO
From $810 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 $810 per night (USD)
VRBO
From $408 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 $408 per night (USD)
VRBO
From $460 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 $460 per night (USD)
VRBO
From $1392 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 $1392 per night (USD)
Expedia
From $769 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 $769 per night (USD)
VRBO
From $1089 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 $1089 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 $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 $411 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 $411 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 $1486 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 $1486 per night (USD)
VRBO
From $683 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 $683 per night (USD)
VRBO
From $1706 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 $1706 per night (USD)
VRBO
From $605 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 $605 per night (USD)
Expedia
From $453 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 $453 per night (USD)
VRBO
From $910 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 $910 per night (USD)
VRBO
From $606 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 $606 per night (USD)
VRBO
From $414 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 $414 per night (USD)
VRBO
From $855 per night (USD)
VRBO
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)
VRBO
From $761 per night (USD)
Expedia
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 $761 per night (USD)
Expedia
$Privacy!! Heated salt-water pool, central a\/c, all kinds of families welcome$
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 $202 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 $202 per night (USD)
VRBO
From $229 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 $229 per night (USD)
VRBO
From $353 per night (USD)
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 ...
From $353 per night (USD)
Expedia
From $304 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 $304 per night (USD)
VRBO
From $939 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 $939 per night (USD)
VRBO
From $492 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 $492 per night (USD)
VRBO
From $424 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 $424 per night (USD)
Expedia
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 $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 $483 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 $483 per night (USD)
VRBO
From $1060 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 $1060 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 $805 per night (USD)
Expedia
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 $805 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
$Charming Farmhouse with Pool and Large Yard \nCentrally Located and Walkable$
From $595 per night (USD)
VRBO
Charming Farmhouse with Pool and Large Yard \nCentrally Located and Walkable
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Walking distance from the Jitney, LIRR & Southold Village. Deck, massive barbecue, indoor soaking tub & outdoor shower. ...
From $595 per night (USD)
VRBO
From $1259 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 $1259 per night (USD)
VRBO
From $317 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 $317 per night (USD)
VRBO
From $742 per night (USD)
Expedia
Country BEACH home!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Perfection!! Amazing, centrally 🌊 located getaway in the middle of EVERYTHING that the North🍷Fork has to offer. BEAUT ...
From $742 per night (USD)
Expedia
From $860 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 $860 per night (USD)
VRBO
From $530 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 $530 per night (USD)
VRBO
From $1442 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 $1442 per night (USD)
VRBO
From $2258 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 $2258 per night (USD)
VRBO
Click For Pricing
VRBO
Historic cottage near the NoFo beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
We are renting our warm, wonderful and rustic 3 bedroom cottage in Southold for parts of July and August. We are steps f ...
Click For Pricing
VRBO
From $290 per night (USD)
VRBO
House central to North Fork wineries restaurants + beaches. Walk to town.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Comfortable House on a quiet private road 0.5 mile to Southold town center. Would work well for a small family or two co ...
From $290 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 $316 per night (USD)
Expedia
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 $316 per night (USD)
Expedia
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 $412 per night (USD)
VRBO
SPRING DISCOUNT - COTTAGE ON LONG ISLAND SOUND, PRIVATE BEACH, GLORIOUS SUNSETS
Bedrooms:
3
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 $412 per night (USD)
VRBO

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Results: 186 Rentals