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 $482 per night (USD)
VRBO
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 $482 per night (USD)
VRBO
From $1412 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 $1412 per night (USD)
VRBO
From $954 per night (USD)
VRBO
Greenport Getaway the perfect blend of relaxation, nature, and North Fork charm.
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
🏡 Charming Family Getaway with Heated Pool, Private Beach Access & Kayaks in Greenport 5 Bedrooms • 4 Bathrooms • Slee ...
From $954 per night (USD)
VRBO
From $879 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 $879 per night (USD)
VRBO
From $769 per night (USD)
VRBO
Greenport Walk to beach & vineyard from this brand new home
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Take it easy at this brand new unique retreat. Walking to distance to the beach and winery. Less than a 2 minute drive ...
From $769 per night (USD)
VRBO
Click For Pricing
Expedia
Beautiful private home with beach access down the block
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
1/2 acre fenced property. open floor plan. Master with en suite bathroom. additional bedrooms and bathrooms for your use ...
Click For Pricing
Expedia
From $983 per night (USD)
VRBO
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 $983 per night (USD)
VRBO
Click For Pricing
Expedia
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 ...
Click For Pricing
Expedia
From $1280 per night (USD)
VRBO
North Fork Waterfront 4-bedroom Home w/Pool & Dock
Bedrooms:
5
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 $1280 per night (USD)
VRBO
From $2550 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 $2550 per night (USD)
VRBO
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 $617 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 $617 per night (USD)
VRBO
From $1249 per night (USD)
VRBO
Sandy Bay Beach
Bedrooms:
1
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)
VRBO
From $283 per night (USD)
Expedia
Lake House Located Near North Fork Wineries
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This ranch house is beautifully located on a freshwater lake in the heart of Long Island's wine country, just minutes fr ...
From $283 per night (USD)
Expedia
From $225 per night (USD)
VRBO
Secluded Lakefront Cottage Near Town Beaches and North Fork Wineries
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This cottage is beautifully located on Great Pond on one-half acre in the heart of Long Island's North Fork. The lakefro ...
From $225 per night (USD)
VRBO
From $914 per night (USD)
VRBO
Serenity on the North Fork
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Mediterranean style newly renovated home on a private waterfront property. Enjoy beautiful sunsets and views of the Lon ...
From $914 per night (USD)
VRBO
From $382 per night (USD)
VRBO
North Fork Retreat
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Keep it simple at this peaceful and centrally-located light filled north fork cottage. Creek views with large yard and m ...
From $382 per night (USD)
VRBO
From $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
Click For Pricing
VRBO
LI Sound view, walk to beaches,lake access/kayaking, fishing
Bedrooms:
1
Bathrooms:
2
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 ...
Click For Pricing
VRBO
Click For Pricing
Expedia
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 ...
Click For Pricing
Expedia
From $1023 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 $1023 per night (USD)
VRBO
From $464 per night (USD)
Expedia
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)
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 $1120 per night (USD)
Expedia
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 $1120 per night (USD)
Expedia
From $142 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 $142 per night (USD)
VRBO
From $670 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 $670 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 $394 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 $394 per night (USD)
Expedia
From $442 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 $442 per night (USD)
VRBO
From $410 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 $410 per night (USD)
Expedia
From $442 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 $442 per night (USD)
VRBO
From $977 per night (USD)
VRBO
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)
VRBO
From $470 per night (USD)
VRBO
SPRING DISCOUNT - COTTAGE ON LONG ISLAND SOUND, PRIVATE BEACH, GLORIOUS SUNSETS
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
This charming cedar shingled beach cottage is located steps away from Long Island Sound with stairs leading down to its ...
From $470 per night (USD)
VRBO
Click For Pricing
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, ...
Click For Pricing
Expedia
From $593 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 $593 per night (USD)
VRBO
From $1238 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 $1238 per night (USD)
Expedia
From $1664 per night (USD)
VRBO
STATELY, PEACEFUL & TASTEFUL WITH SPARKLING POOL
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 $1664 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 $1429 per night (USD)
VRBO
Waterfront Historic Artist’s Home, with private beach, sleeps 10
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Beachfront Historic Artist’s Residence If you’re looking for 2 to 3 amazing weeks in prime vacation time, August 22 ...
From $1429 per night (USD)
VRBO
From $1114 per night (USD)
VRBO
Sandpoint by Rove Travel Modern 5BR Family Home with 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 $1114 per night (USD)
VRBO
From $384 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 $384 per night (USD)
VRBO
From $520 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 $520 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
Click For Pricing
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 ...
Click For Pricing
Expedia
From $953 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 $953 per night (USD)
VRBO
$Charming Farmhouse with Pool and Large Yard \nCentrally Located and Walkable$
From $858 per night (USD)
VRBO
Charming Farmhouse with Pool and Large Yard \nCentrally Located and Walkable
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Walking distance from the Jitney, LIRR & Southold Village. Deck, massive barbecue, indoor soaking tub & outdoor shower. ...
From $858 per night (USD)
VRBO
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:
3
Bathrooms:
5
Sleeps:
10
Amidst north fork wineries steps from sandy beach. Private dock, kayaks, paddle board, private community. Spacious 5 b ...
From $1734 per night (USD)
Expedia
From $856 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 $856 per night (USD)
VRBO
Click For Pricing
Expedia
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
Expedia
From $583 per night (USD)
VRBO
Updated Historic shingle-style 1902 4-bedroom Beach House on Southold Bay!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
You are invited to have a wonderful time in this Southold, Long Island beach house. You will have a fabulous time of sun ...
From $583 per night (USD)
VRBO
From $712 per night (USD)
Expedia
Waterfront home with private beach amazing view and sleeps 12 !
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 $712 per night (USD)
Expedia
$Southold retreat-- Indoor/outdoor living near immaculate beaches & wineries\n\n\n\n$
From $477 per night (USD)
VRBO
Southold retreat-- Indoor/outdoor living near immaculate beaches & wineries\n\n\n\n
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your perfect summer getaway located in the desirable Claves Neck neighborhood, minutes from northfork's great ...
From $477 per night (USD)
VRBO
From $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 $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 $3381 per night (USD)
Expedia
Luxury north fork estate
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Absolutely stunning custom home Italian Tuscan style villa on the outside. Modern Hamptons vibe on the inside . 1 acre + ...
From $3381 per night (USD)
Expedia
From $1117 per night (USD)
VRBO
NORTH FORK DREAM HOME, 4,000 Sq Ft, 1 Acre, Heated Pool!
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Make yourself at home in this spacious and beautiful North Fork Wine Country home in the heart of Southold! This 4,000 s ...
From $1117 per night (USD)
VRBO
From $979 per night (USD)
VRBO
Stylish beach getaway: pool in prime location
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to our beautifully renovated, designer-decorated home in the heart of Southold, NY! Perfectly located within wal ...
From $979 per night (USD)
VRBO
From $789 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 $789 per night (USD)
VRBO
From $551 per night (USD)
Expedia
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 $551 per night (USD)
Expedia
From $870 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 $870 per night (USD)
VRBO
From $1587 per night (USD)
VRBO
Spacious Home with Pool in Southold
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Discover this sun-filled 4-bedroom Southold home, perfect for a relaxing escape. Enjoy a luxurious saltwater pool, cozy ...
From $1587 per night (USD)
VRBO
From $606 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 $606 per night (USD)
VRBO
From $363 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 $363 per night (USD)
VRBO
From $813 per night (USD)
VRBO
Country BEACH home!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Perfection!! Amazing, centrally 🌊 located getaway in the middle of EVERYTHING that the North🍷Fork has to offer. BEAUT ...
From $813 per night (USD)
VRBO
From $538 per night (USD)
VRBO
Expansive North Fork Estate on almost 3 Acres, Close to Vineyards and...
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Please note that a reservation for this property needs to be approved before it is confirmed. North Fork Farmhouse Exp ...
From $538 per night (USD)
VRBO
From $655 per night (USD)
VRBO
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 $655 per night (USD)
VRBO
From $442 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 $442 per night (USD)
VRBO
From $606 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 $606 per night (USD)
VRBO
From $925 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 $925 per night (USD)
Expedia
From $1168 per night (USD)
VRBO
Beautifully farmhouse
Bedrooms:
3
Bathrooms:
5
Sleeps:
7
<p>A short distance from ice skating, sailing, and more, this family-friendly vacation home lets you experience it all. ...
From $1168 per night (USD)
VRBO
From $723 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 $723 per night (USD)
VRBO
From $629 per night (USD)
VRBO
Renovated 1930's cottage on the water near Greenport with WiFi, AC
Bedrooms:
1
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 $718 per night (USD)
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 ...
From $718 per night (USD)
Expedia
From $946 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 $946 per night (USD)
VRBO
From $217 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 $217 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 $1866 per night (USD)
VRBO
Resort-Style Southold Retreat with Private Pool, Guest House, and Chic...
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Please note that a reservation for this property needs to be approved before it is confirmed. The Southold Escape Reso ...
From $1866 per night (USD)
VRBO
From $680 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 $680 per night (USD)
VRBO
From $623 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 $623 per night (USD)
VRBO
From $1269 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 $1269 per night (USD)
VRBO
From $599 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 $599 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 $1120 per night (USD)
Expedia
Chic North Fork Getaway with Resort-Style Pool & Stylish Interiors
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
North Fork Dream Chic North Fork Getaway with Resort-Style Pool & Stylish Interiors 4BR/3.5BA: Private pool, plush cha ...
From $1120 per night (USD)
Expedia

Search Your Destination Now!

Southold Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 184 Rentals