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 $554 per night (USD)
VRBO
NF Wine Country Retreat with Dock
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Enjoy this idyllic family friendly home in the heart of North Fork, Long Island. It's a newly renovated and spacious 4 b ...
From $554 per night (USD)
VRBO
From $419 per night (USD)
Expedia
Family and Dog friendly, private beach⛱️ Amazing Wineries within minutes!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This house is beautifully decorated and comfortable, light and spacious with it's wooden floors throughout with every a ...
From $419 per night (USD)
Expedia
From $1795 per night (USD)
VRBO
Contemporary Colonial home with pristine Peconic bay views, steps to...
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Vineyard Beach House Contemporary Colonial home with pristine Peconic bay views, steps to private beach, Weber grill, f ...
From $1795 per night (USD)
VRBO
From $736 per night (USD)
Expedia
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 $736 per night (USD)
Expedia
From $1107 per night (USD)
VRBO
6 BR. Saltwater Pool, Hot tub, sauna, walk to beach, minutes to vineyards, town!
Bedrooms:
3
Bathrooms:
6
Sleeps:
10
Welcome to our modern beach house, boasting all the amenities you could ask for including 6 Bedrooms and 3 Full Baths, a ...
From $1107 per night (USD)
VRBO
From $474 per night (USD)
Expedia
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 $474 per night (USD)
Expedia
From $1867 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 $1867 per night (USD)
VRBO
From $933 per night (USD)
Expedia
Greenport 'Sunshine Home'
Bedrooms:
4
Bathrooms:
7
Sleeps:
10
This welcoming colonial is situated on three-fourths of an acre. Family friendly, the house is perfect for your time awa ...
From $933 per night (USD)
Expedia
From $805 per night (USD)
VRBO
Coastal Getaway, water views, walk to beach
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Coastal Vibes: Home with waterviews, short distance from a secluded beach on Pipes Cove overlooking Shelter Island. Bea ...
From $805 per night (USD)
VRBO
From $748 per night (USD)
Expedia
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 $748 per night (USD)
Expedia
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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 ...
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VRBO
From $1266 per night (USD)
Expedia
Amazing Beach House in the North Fork Wineries
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Heart of wine country, steps from the beach, minutes to Greenport. Spacious 3 bedroom/ 2.5 bath boasts vaulted ceilings ...
From $1266 per night (USD)
Expedia
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VRBO
Southold by the bay
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Beautiful ranch style home within walking distance of the beach. Has a large backyard and deck for entertaining. Featur ...
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VRBO
$North Fork Waterfront 4-bedroom Home w\/Pool & Dock$
From $1755 per night (USD)
Expedia
North Fork Waterfront 4-bedroom Home w\/Pool & Dock
Bedrooms:
6
Bathrooms:
4
Sleeps:
10
The whole family will enjoy this waterfront home with lots of room for fun. Pool, dock and large great room offers ample ...
From $1755 per night (USD)
Expedia
From $2605 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 $2605 per night (USD)
VRBO
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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 ...
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Expedia
From $663 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 $663 per night (USD)
VRBO
From $1249 per night (USD)
Expedia
Sandy Bay Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Stunning waterfront location with amazing sugar sand beach! Well proportioned home with beautiful symmetry. The centra ...
From $1249 per night (USD)
Expedia
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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 ...
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VRBO
From $331 per night (USD)
Expedia
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 $331 per night (USD)
Expedia
From $914 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 $914 per night (USD)
VRBO
From $399 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 $399 per night (USD)
Expedia
From $730 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 $730 per night (USD)
VRBO
$LI Sound view, walk to beaches,lake access\/kayaking, fishing$
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Expedia
LI Sound view, walk to beaches,lake access\/kayaking, fishing
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
Water views from every room of LI Sound and Great Pond. Walk to beautiful sound beaches and watch the sunset from the de ...
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Expedia
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VRBO
Private Guest Room-heart of Long Island's North Fork wine country-steps to beach
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Small clean guestroom with private entrance and private bath located on private road with minimal traffic. Free onsite p ...
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VRBO
From $1164 per night (USD)
Expedia
North Fork Waterfront Spectacular Views Cottage circa 1930
Bedrooms:
1
Bathrooms:
4
Sleeps:
10
North Fork Waterfront Spectacular Views Cottage circa 1930' On Golden Pond' Private road, amazing waterfront vie ...
From $1164 per night (USD)
Expedia
From $1067 per night (USD)
VRBO
Newly Renovated Gem on the Cedar Beach Peninsula!
Bedrooms:
5
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 $1067 per night (USD)
VRBO
From $464 per night (USD)
Expedia
Beautiful North Fork 3-Bedroom Home Steps Away from a Private Sandy Bay
Bedrooms:
3
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 $464 per night (USD)
Expedia
From $1145 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 $1145 per night (USD)
VRBO
From $1621 per night (USD)
Expedia
Gorgeous Greenport Beach House right on the Sound! Breathtaking views
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to Villa Sonore. A gorgeous beachfront home in Greenport located right on the LI Sound. Walk to restaurants and ...
From $1621 per night (USD)
Expedia
$Southold Cottage w\/ Patio & Grill - Walk to Beach!$
From $140 per night (USD)
VRBO
Southold Cottage w\/ Patio & Grill - Walk to Beach!
Bedrooms:
1
Bathrooms:
3
Sleeps:
3
If you’re a nature lover, a beach lover, a wine lover, or just in need of an escape, plan your dates for a stay at this ...
From $140 per night (USD)
VRBO
$Serene bay front home with a private beach, deck, board games, & washer\/dryer$
From $686 per night (USD)
Expedia
Serene bay front home with a private beach, deck, board games, & washer\/dryer
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Watersedge Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $686 per night (USD)
Expedia
From $695 per night (USD)
VRBO
Warm Peconic home…short walk to a private beach.
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Minimum 14 day rental required (as per Town of Southold) Quaint cozy quiet private road short walk to sandy private bea ...
From $695 per night (USD)
VRBO
From $660 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 $660 per night (USD)
Expedia
From $698 per night (USD)
VRBO
Vine + Sand--Southold, NY'S Newest B&B--Room 2--King 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 B ...
From $698 per night (USD)
VRBO
From $635 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 $635 per night (USD)
Expedia
From $714 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 $714 per night (USD)
VRBO
From $977 per night (USD)
Expedia
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 $977 per night (USD)
Expedia
From $454 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 $454 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 $714 per night (USD)
VRBO
Secluded charmer with gunnite & saltwater pool, stone fireplace steps to beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Built in 1928, this gorgeous shingled home is fully equipped to host your getaway. You're within easy walking distance o ...
From $714 per night (USD)
VRBO
From $1701 per night (USD)
Expedia
Well-appointed coastal home with large yard, pool, basketball, & outdoor kitchen
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Secret Garden Estate Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $1701 per night (USD)
Expedia
From $322 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 $322 per night (USD)
VRBO
From $1618 per night (USD)
Expedia
STATELY, PEACEFUL & TASTEFUL WITH SPARKLING POOL AND FIREPLACES
Bedrooms:
4
Bathrooms:
4
Sleeps:
7
Beautiful home on gorgeous tree-lined street in Southold on the North Fork, Long Island. Near Greenport, Orient, Shelter ...
From $1618 per night (USD)
Expedia
From $1388 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 $1388 per night (USD)
VRBO
From $1540 per night (USD)
Expedia
Sandpoint by Rove Travel Modern 5BR Family Home with Pool
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
Summary: Welcome to Sandpoint, a Rove Travel Home! Rove offers curated, luxury residences with the quality and care of ...
From $1540 per night (USD)
Expedia
From $405 per night (USD)
VRBO
Lovely 4 Bedroom Southold Home Walking Distance to Peconic Bay
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Beautiful and quiet corner home in a lovely neighborhood in Southold. 100 year old farmhouse but with modern convenienc ...
From $405 per night (USD)
VRBO
From $1551 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 $1551 per night (USD)
Expedia
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VRBO
Farmhouse Oasis with Vineyard Views
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Unwind and soak in summer at this incredibly charming North Fork farmhouse. Private back yard with in-ground heated poo ...
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VRBO
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Expedia
Palm Springs Vibes on the North Fork
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Feel the happy vibes of Palm Springs with a fully guy renovated ranch home on an acre of land. Brand new appliances. Clo ...
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Expedia
From $1228 per night (USD)
VRBO
Modern North Fork Haven: Beachfront, Heated Pool
Bedrooms:
4
Bathrooms:
4
Sleeps:
9
Summary: As you step into this charming stunning and newly constructed home beachfront oasis, you'll be greeted by a spa ...
From $1228 per night (USD)
VRBO
$Charming Farmhouse with Pool and Large Yard \nCentrally Located and Walkable$
From $875 per night (USD)
Expedia
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 $875 per night (USD)
Expedia
From $686 per night (USD)
VRBO
Another rental season is coming up.
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Hi everyone: I hope you'll look at the photos of our property and our guest reviews. But please allow me to say we do ha ...
From $686 per night (USD)
VRBO
From $1734 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 $1734 per night (USD)
Expedia
From $940 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 $940 per night (USD)
VRBO
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Expedia
North Fork Waterfront Home - Lots of Room - Luxurious Comfort
Bedrooms:
4
Bathrooms:
6
Sleeps:
10
Waterfront private dock-Luxury comfort on North Fork -perfect for family fun-Lots of room Amenities include newly renova ...
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Expedia
From $724 per night (USD)
VRBO
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 $724 per night (USD)
VRBO
From $1205 per night (USD)
Expedia
Waterfront home with private beach on property!
Bedrooms:
4
Bathrooms:
6
Sleeps:
10
"Baydreams" is an amazing bayfront home ready for rent to create memories! Walk out onto the large deck which extends to ...
From $1205 per night (USD)
Expedia
$Southold retreat-- Indoor\/outdoor living near immaculate beaches & wineries\n\n\n\n$
From $498 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 $498 per night (USD)
VRBO
From $1142 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 $1142 per night (USD)
Expedia
From $569 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 $569 per night (USD)
VRBO
From $3493 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 $3493 per night (USD)
Expedia
From $1818 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 $1818 per night (USD)
VRBO
From $979 per night (USD)
Expedia
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)
Expedia
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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 ...
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VRBO
From $685 per night (USD)
Expedia
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 $685 per night (USD)
Expedia
From $456 per night (USD)
VRBO
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 $456 per night (USD)
VRBO
From $1271 per night (USD)
Expedia
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 $1271 per night (USD)
Expedia
From $1526 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 $1526 per night (USD)
VRBO
From $974 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 in Southold. With amenities like gourmet kitchen, AC, WiFi, chi ...
From $974 per night (USD)
Expedia
From $393 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 $393 per night (USD)
VRBO
From $847 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 $847 per night (USD)
Expedia
From $1475 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 $1475 per night (USD)
VRBO
From $1289 per night (USD)
Expedia
Spacious North Fork Home in Greenport, Heated Pool, Perfect for Families
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Greenport Cove Contemporary Spacious North Fork Home in Greenport, Heated Pool, Perfect for Families 4BR/3.5BA: privat ...
From $1289 per night (USD)
Expedia
From $527 per night (USD)
VRBO
Waterfront Greenport Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This two-bedroom, two-bathroom condo at Cliffside Resort offers a serene escape with breathtaking views of the Long Isla ...
From $527 per night (USD)
VRBO
From $1127 per night (USD)
Expedia
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 $1127 per night (USD)
Expedia
From $512 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 $512 per night (USD)
VRBO
From $956 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 $956 per night (USD)
Expedia
From $676 per night (USD)
VRBO
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 $676 per night (USD)
VRBO
From $555 per night (USD)
Expedia
Beautiful Waterview Condo on the North Fork of LI
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Waterview luxury suite accommodates up to 6 guests with two bedrooms and two bathrooms located on the North Fork of Long ...
From $555 per night (USD)
Expedia
From $629 per night (USD)
VRBO
Renovated 1930's cottage on the water near Greenport with WiFi, AC
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Escape to a charming 3-bedroom cottage on Breezy Shores located between Greenport and Southold. This lovely retreat feat ...
From $629 per night (USD)
VRBO
From $821 per night (USD)
Expedia
Sea Breeze Paradise: Beachfront & Panoramic Views
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Summary: Sea Breeze Paradise is a newly renovated home. A paradise for those of you who want to enjoy the sun and fresh ...
From $821 per night (USD)
Expedia
From $1040 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 $1040 per night (USD)
VRBO
From $236 per night (USD)
Expedia
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 $236 per night (USD)
Expedia
From $386 per night (USD)
VRBO
Charming 2-bedroom home with AC in the heart of Wine Country
Bedrooms:
1
Bathrooms:
2
Sleeps:
8
Stay comfortably in Southold at this 2-bedroom home. This gorgeous property features 1 queen bed and one full over queen ...
From $386 per night (USD)
VRBO

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Results: 185 Rentals