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 $283 per night (USD)
VRBO
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 $283 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 $635 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 $635 per night (USD)
VRBO
From $879 per night (USD)
VRBO
Newly Renovated Gem on the Cedar Beach Peninsula!
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Come and experience the peaceful tranquility of the North Fork with this newly renovated gem in the heart of Southold. I ...
From $879 per night (USD)
VRBO
From $464 per night (USD)
VRBO
Beautiful North Fork 3-Bedroom Home Steps Away from a Private Sandy Bay
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beautiful vacation home in the Bay Haven community of Southold. The house is on a fully landscaped property of over a th ...
From $464 per night (USD)
VRBO
From $1145 per night (USD)
Expedia
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)
Expedia
From $1089 per night (USD)
VRBO
Gorgeous Greenport Beach House right on the Sound! Breathtaking views
Bedrooms:
2
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 $1089 per night (USD)
VRBO
From $238 per night (USD)
VRBO
Southold Cottage w/ Patio & Grill - Walk to Beach!
Bedrooms:
1
Bathrooms:
2
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 $238 per night (USD)
VRBO
From $668 per night (USD)
VRBO
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 $668 per night (USD)
VRBO
From $696 per night (USD)
Expedia
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 $696 per night (USD)
Expedia
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 $580 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 $580 per night (USD)
VRBO
From $1314 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 $1314 per night (USD)
VRBO
From $1011 per night (USD)
VRBO
Sandpoint by Rove Travel | 6BR Family Home w/ Pool
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
Summary: Welcome to Sandpoint, a Rove Travel Home! Rove offers curated, luxury residences with the quality and care of ...
From $1011 per night (USD)
VRBO
From $395 per night (USD)
VRBO
Lovely 4 Bedroom Southold Home Walking Distance to Peconic Bay
Bedrooms:
1
Bathrooms:
4
Sleeps:
6
Beautiful and quiet corner home in a lovely neighborhood in Southold. 100 year old farmhouse but with modern convenienc ...
From $395 per night (USD)
VRBO
From $389 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 $389 per night (USD)
VRBO
Click For Pricing
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 ...
Click For Pricing
VRBO
From $785 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 $785 per night (USD)
VRBO
From $514 per night (USD)
VRBO
I’ve had the best guests!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Hi everyone: I’d like to sincerely thank all the great guests that stayed at our home, and those of you who viewed the l ...
From $514 per night (USD)
VRBO
From $810 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 $810 per night (USD)
Expedia
Click For Pricing
VRBO
North Fork Waterfront Home - Lots of Room - Luxurious Comfort
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Waterfront private dock-Luxury comfort on North Fork -perfect for family fun-Lots of room Amenities include newly renova ...
Click For Pricing
VRBO
From $543 per night (USD)
Expedia
Updated Historic shingle-style 1902 4-bedroom Beach House on Southold Bay!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
You are invited to have a wonderful time in this Southold, Long Island beach house. You will have a fabulous time of sun ...
From $543 per night (USD)
Expedia
From $797 per night (USD)
VRBO
Waterfront home with private beach amazing view and sleeps 10 !
Bedrooms:
3
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 $797 per night (USD)
VRBO
$Southold retreat-- Indoor/outdoor living near immaculate beaches & wineries\n\n\n\n$
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)
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
From $1809 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 $1809 per night (USD)
VRBO
From $739 per night (USD)
VRBO
“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 $739 per night (USD)
VRBO
From $464 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 $464 per night (USD)
VRBO
From $570 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 $570 per night (USD)
VRBO
From $741 per night (USD)
Expedia
Country BEACH home!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Perfection!! Amazing, centrally 🌊 located getaway in the middle of EVERYTHING that the North🍷Fork has to offer. BEAUT ...
From $741 per night (USD)
Expedia
From $399 per night (USD)
VRBO
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 $399 per night (USD)
VRBO
From $513 per night (USD)
Expedia
Spacious North Fork Home in Greenport, Heated Pool, Perfect for Families
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Greenport Cove Contemporary Spacious North Fork Home in Greenport, Heated Pool, Perfect for Families 4BR/3.5BA: privat ...
From $513 per night (USD)
Expedia
From $425 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 $425 per night (USD)
VRBO
From $417 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 $417 per night (USD)
Expedia
From $922 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 $922 per night (USD)
VRBO
From $1168 per night (USD)
Expedia
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 $1168 per night (USD)
Expedia
From $674 per night (USD)
VRBO
Beautiful Waterview Condo on the North Fork of LI
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Waterview luxury suite accommodates up to 6 guests with two bedrooms and two bathrooms located on the North Fork of Long ...
From $674 per night (USD)
VRBO
Click For Pricing
Expedia
Sea Breeze Paradise: Beachfront & Panoramic Views
Bedrooms:
2
Bathrooms:
3
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 ...
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Expedia
From $241 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 $241 per night (USD)
VRBO
From $428 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 $428 per night (USD)
VRBO
From $698 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 $698 per night (USD)
VRBO
From $565 per night (USD)
VRBO
Peconic Retreat: Charming Home, Across from Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Nestled in the heart of Peconic, this charming mid-century home offers a peaceful retreat on Long Island’s Nort ...
From $565 per night (USD)
VRBO
From $1568 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 $1568 per night (USD)
VRBO
From $515 per night (USD)
Expedia
Newly Renovated, Stylish Peconic Retreat with Private Pool, Lush Grounds,...
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
North Fork Chic Newly Renovated, Stylish Peconic Retreat with Private Pool, Lush Grounds, Perfect for Families. 4BR/2. ...
From $515 per night (USD)
Expedia
From $714 per night (USD)
VRBO
Spacious Vacation 4BR Home Near Southold Beach, Greenport, and Top Wineries
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Enjoy a relaxing North Fork getaway in this spacious vacation rental, ideally located just minutes from Southold Town Be ...
From $714 per night (USD)
VRBO
From $219 per night (USD)
Expedia
Surrounded by nature, come stay in this 1 bedroom private, serene location
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Quiet location, surrounded by trees and nature, a pond on the property that brings the beautiful sounds of nature to hel ...
From $219 per night (USD)
Expedia
From $686 per night (USD)
VRBO
Mid-Century Gem with Pool, Fireplace and Steps to Private Beach.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to our stylish mid-century modern retreat on Shelter Island. A 90 second walk to stunning Crab Creek and a privat ...
From $686 per night (USD)
VRBO
Click For Pricing
Expedia
Southold Waterfront Home with Outdoor Adventures & Scenic Views
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
This charming 4-bedroom home in Southold is the perfect retreat for your next getaway. With 1 king bed, 2 queen beds, an ...
Click For Pricing
Expedia

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Southold Rentals

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Results: 148 Rentals