Compare best Airbnb in Southold, NY from 100+ providers!
213 available vacation rental offers
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating
Best Vacation rentals and Airbnb offers in Southold, NY
9.5 30 reviews
Southold, NY
07/05 – 07/09
$1636/nighttotal: $6544 (4 )
North Fork Resort
3 4
resort , Greenport
Resort with an excellent rating of 95% based on 30 reviews. You will be based in Greenport. Facilities and services include air conditioning, a garden and a barbecue. This is a family-friendly resort!
Southold, NY
07/05 – 07/09
$2357/nighttotal: $9428 (4 )
Spacious Open Design For Summer '26 Dates
4 4
apartment , Noyack
This Sag Harbor rental is conveniently located near Cooper's Beach and the Sag Harbor Whaling and Historical Museum, offering easy access to Hamptons attractions. The four-bedroom, four-bathroom home sleeps fourteen guests and features a large open kitchen, outdoor BBQ, and an additional office space with a futon, perfect for large groups seeking a comfortable and stylish stay.
Southold, NY
07/05 – 07/09
$2525/nighttotal: $10100 (4 )
Luxury Sag Harbor Home With Heated Pool & Charm
4 4
apartment , Bridgehampton
This Sag Harbor estate is located near village shops and dining, a short 2-mile drive from the beach, and within proximity to local landmarks like the North Main Street Historic District and Havens House. This 3000 sq ft residence offers 4 bedrooms and 3 bathrooms to accommodate 8 guests, featuring a private heated pool, a chef's kitchen, a media room, and an outdoor dining area with a BBQ grill.
10 4 reviews
Southold, NY
07/05 – 07/09
$2280/nighttotal: $9120 (4 )
Spacious North Fork Home In Greenport, Heated Pool, Perfect For Families
4 4
apartment , Shelter Island Heights
This four-bedroom, 3.5-bathroom house rental in Greenport, on Long Island's North Fork, is a short drive from Shelter Island Heights and offers easy access to beaches like HOA Beach and Southold Town Beach. The 4-bedroom home features a private heated pool and hot tub, multiple indoor/outdoor dining areas, a dedicated workspace, a gas BBQ, and accommodates up to eight guests; StayMarquis management provides 24/7 support.
9.9 79 reviews
Southold, NY
07/05 – 07/09
$783/nighttotal: $3132 (4 )
Brand New 2 Bedroom, Greenport Village, Walk To Town Marina Views!!
2 4
apartment , Greenport
This vacation home in Greenport is located within walking distance of the Greenport Farmers' Market, Eastern Long Island Hospital, and Stony Brook Eastern Long Island Hospital, offering a convenient and central location. It has excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay. The home features a fully equipped kitchen, laundry facilities, free Wi-Fi, a Smart TV, a garden, and barbecue grills. Guests can enjoy outdoor relaxation, prepare their own meals, and stay connected during their stay.
10 10 reviews
Southold, NY
07/05 – 07/09
$1140/nighttotal: $4560 (4 )
Luxury By The Sea
4 4
apartment , Southold
This Southold vacation home is located within 3 miles of five prestigious wineries—Croteaux, Mattebella, Corey Creek, Sparkling Pointe, and Sannino's Bella Vita—perfect for wine tasting. This three-bedroom, three-bathroom house sleeps eight guests comfortably, offering amenities such as a fully equipped kitchen, free Wi-Fi, a fireplace, barbecue grills, and air conditioning.
10 3 reviews
Southold, NY
07/05 – 07/09
$2005/nighttotal: $8020 (4 )
New Construction Greenport Pool House - 3 Blocks From Town
4 4
house , Greenport
This Greenport villa is a short walk from the Greenport Farmers' Market, Railroad Museum of Long Island, and Camera Obscura, offering easy access to the town's attractions. The area is known for its charming shops, restaurants, and waterfront views. This 2,700 square foot home has three bathrooms, providing ample space for families or groups. Enjoy a private pool, spa tub, outdoor patio, and a fully equipped kitchen with modern amenities, including free WiFi.
Southold, NY
07/05 – 07/09
$3442/nighttotal: $13768 (4 )
Villa Ebrar - Luxury With Pool
4 4
house , Noyack
This 4-bedroom villa is situated in Sag Harbor, just a short drive from Foster Memorial Beach and Montauk Point Lighthouse, offering easy access to the area's attractions. It has received excellent user ratings, making it a popular choice for travelers. The 3,000 square foot house offers ample space for families and groups. Enjoy a private pool, a fully equipped kitchen, and a terrace, plus amenities like a tennis court, parking, and room service.
9.9 61 reviews
Southold, NY
07/05 – 07/09
$994/nighttotal: $3976 (4 )
Brand New Charming Beach House
4 4
apartment , Mattituck
This vacation home is located in Mattituck, within a 3-mile radius of several renowned wineries, making it ideal for wine enthusiasts. The house boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay. The home features four bedrooms and two bathrooms, comfortably accommodating up to 10 guests. Guests can enjoy amenities like a fully equipped kitchen, a fireplace, a barbecue grill, and a smoke-free environment, allowing for a relaxing and enjoyable experience.
10 5 reviews
Southold, NY
07/05 – 07/09
$810/nighttotal: $3240 (4 )
Northfork Townhouse Walk To All
4 4
apartment , Greenport
This 3-bedroom house is conveniently located in central Greenport, within a 10-minute walk of the Greenport Farmers' Market, Railroad Museum of Long Island, and Camera Obscura. The home comfortably accommodates 6 guests and offers a fully equipped kitchen, outdoor barbecue grills, a garden, and free WiFi.
Southold, NY
07/05 – 07/09
$1507/nighttotal: $6028 (4 )
3-bedroom House On Main Street Sag Harbor Village
3 4
apartment , Sag Harbor
This 3-bedroom, 2-bathroom Sag Harbor apartment offers a prime location within Sag Harbor Village, providing convenient access to The Hamptons Beaches and Cooper's Beach, both less than 2 miles away, and is also within easy reach of the Sag Harbor Whaling and Historical Museum and Bay Street Theatre. This well-appointed rental accommodates up to 6 guests and features air conditioning and internet, with a spacious primary suite and three comfortable bedrooms for ample sleeping arrangements.
Southold, NY
07/05 – 07/09
$5452/nighttotal: $21808 (4 )
Spacious 5-bedroom House With Water Views And 2 Houses From The Bay.
5 4
apartment , North Haven
This Sag Harbor vacation home, near Bay Street Theatre and the Sag Harbor Whaling and Historical Museum, offers easy access to Eastville Heritage House and Havens House. This five-bedroom, six-bathroom house sleeps ten guests, boasting a private guest area, smart TVs in all bedrooms, a pool, and proximity to Sag Harbor attractions like BookHampton and Shelter Island.
Best Southold, NY vacation rentals with a balcony
10 6 reviews
Southold, NY
07/05 – 07/09
$2043/nighttotal: $8172 (4 )
Spacious And Modern North Fork Home Close To Multiple Wineries, Perfect For...
3 4
apartment , Cutchogue
This three-bedroom, three-bathroom Cutchogue rental is conveniently located near Peconic Bay Vineyards on the North Fork, offering easy access to the North Fork wine trail and other attractions. The 3-bedroom home features a modern open layout, accommodating up to six guests with amenities including a gas grill, pool table, and foosball table, plus access to StayMarquis services.
Southold, NY
07/05 – 07/09
$4351/nighttotal: $17404 (4 )
Hamptons 9bd Mega Compound W Pool Tennis Bball Nightclub
9 4
house , Noyack
This 9-bedroom villa is located in Noyack, 48 miles from Long Island MacArthur Airport. This spacious residence offers 5010 square feet of living space, accommodating up to 60 guests with amenities including a private pool, hot tub, and a well-equipped kitchen.
10 1 review
Southold, NY
07/05 – 07/09
$8122/nighttotal: $32488 (4 )
Ultimate Hamptons Luxury With Private Tennis And Pool
8 4
apartment , Water Mill
This spacious vacation home is nestled in the serene landscape of Water Mill, offering a tranquil retreat by the river, just a short drive from the vibrant beaches and attractions of the Hamptons. With excellent user ratings, this family-friendly home features 8 bedrooms and 8 bathrooms, comfortably accommodating up to 20 guests. Enjoy the luxury of a private pool, cozy up by the fireplace, and stay connected with complimentary WiFi. The fully equipped kitchen, fitness center, tennis court, and garden with barbecue grills provide ample opportunities for relaxation and recreation.
Southold, NY
07/05 – 07/09
$4680/nighttotal: $18720 (4 )
Villa Zainip - Luxury With Pool
5 4
house , Noyack
Villa Zainip is a luxurious home located in Sag Harbor, just 21 miles from Montauk Point Lighthouse and 26 miles from Splish Splash waterpark. The villa is conveniently located near the beautiful beaches of Sag Harbor, making it a perfect choice for families or groups of friends looking for a relaxing and enjoyable vacation. The villa offers 5 bedrooms, 4 bathrooms, and can comfortably accommodate up to 8 guests. The villa features a private pool and garden, a fully equipped kitchen, a sauna, and free Wi-Fi.
Our Favorite Family-Friendly Vacation Rentals in Southold, NY
These family-friendly vacation rentals in Southold, NY offer spacious layouts and easy access to local beaches.
10 8 reviews
Southold, NY
07/05 – 07/09
$1442/nighttotal: $5768 (4 )
Cozy Greenport Village Cottage
4 4
apartment , Greenport
This family-friendly apartment is situated in the rural Pipes Cove district of Greenport, a 7-minute walk from the Long Island Railroad Museum and an 11-minute walk from the Antique Carousel, with Greenport train station just 9 minutes away. This 1800 square foot vacation home accommodates up to 8 guests and features 4 bedrooms, 4 bathrooms, air conditioning, free Wi-Fi, a full kitchen with an ice dispenser, and outdoor amenities like a fire pit and barbecue.
10 12 reviews
Southold, NY
07/05 – 07/09
$938/nighttotal: $3752 (4 )
Relaxation In Greenport
3 4
apartment , Greenport
This Greenport vacation home is ideally located a 5-minute walk from the Greenport Farmers' Market, Camera Obscura, and Railroad Museum of Long Island, and under 10 minutes from the East End Seaport Maritime Museum and Greenport Carousel. This 1,500-square-foot house features four bedrooms, two bathrooms, accommodates eight guests, and includes a fully equipped kitchen, private patio, free Wi-Fi, and parking.
Southold, NY
07/05 – 07/09
$2125/nighttotal: $8500 (4 )
The Chequit
3 4
island , Shelter Island Heights
The Chequit Hotel is situated in the tranquil surroundings of Shelter Island Heights, within easy reach of the Shelter Island Country Club and the historic Sylvester Manor. The hotel offers 35 cozy guestrooms with blackout drapes for privacy, as well as a range of amenities including an on-site restaurant, coffee shop, free Wi-Fi and self-parking.
10 38 reviews
Southold, NY
07/05 – 07/09
$1256/nighttotal: $5024 (4 )
Perfect Waterfront Family Vacation Home Next To The Best Vineyards In Ny!
3 4
apartment , Southold
This 3-bedroom, 2-bathroom beachfront cottage in Southold offers direct access to a private community beach and is located near the Railroad Museum of Long Island and East End Seaport Maritime Museum, with Croteaux Vineyards and Mattebella Vineyards also nearby. This pet-friendly rental features a kitchen with a fridge, microwave, and dishwasher, air conditioning, a garden, spa, and parking, with opportunities for swimming, boating, and fishing on Goose Creek.
Frequently Asked Questions about vacation rentals in Southold, NY
What are some interesting places to visit in or near Southold, NY?
Southold is a charming town with plenty to see. Visit the historic Southold Historical Society Museum to learn about the area's past. You can also explore the beautiful Long Island Sound, go wine tasting at one of the many vineyards in the area, or visit the Orient Point Ferry Terminal to catch a ferry to the mainland.
What are the best Airbnb and vacation rentals in Southold, NY?
Which walking or cycling routes are the best in Southold, NY?
The Southold Town Park is a great place to go for a walk or bike ride. You can also explore the scenic Southold Bay by bike on the Southold Bay Bike Path. If you want a longer ride, the Peconic Bay Trail runs for miles along the waterfront.
What are the most popular Airbnbs in Southold, NY?
What sports or outdoor activites can visitors enjoy in and around Southold, NY?
Southold is a great place to enjoy the outdoors. You can go fishing, boating, kayaking, swimming, or even go for a hike in the Orient Point State Park. In the summer, you can also enjoy the Southold Farmers Market, which has fresh produce and local crafts.
What are the best vacation rentals with a pool in Southold, NY?
What other towns or cities can be easily accessed from Southold, NY?
Greenport is just a short drive from Southold and is a great place to visit for its shops, restaurants, and harbor. Mattituck is another nearby town known for its wineries and farms. If you want to explore the rest of Long Island, you can easily get to Riverhead, Montauk, and Shelter Island from Southold.
What are the best rentals for families and kids in Southold, NY?
What amenities are commonly available in vacation rentals in Southold, NY?
Vacation rentals in Southold often come with amenities like a kitchen, laundry, and a private patio or balcony. Many also have access to a pool or hot tub. Some rentals even offer waterfront views or access to a dock.
What are the best rentals or Airbnbs with a jacuzzi in Southold, NY?
What time of year is best to rent a vacation rental Southold, NY?
The best time to rent a vacation rental in Southold is during the summer months, from June to August. The weather is warm and sunny, and there are plenty of outdoor activities to enjoy. However, spring and fall can also be beautiful times to visit, with cooler temperatures and fewer crowds.
Destinations nearby
Best Southold, NY vacation rentals with parking
9.9 38 reviews
Southold, NY
07/05 – 07/09
$3646/nighttotal: $14584 (4 )
Stunning Waterfront Estate House With 270 Degree Sea Views On 7 Private Acres
4 4
apartment , Shelter Island Heights
This waterfront Estate House is located on the Menantic Peninsula in Shelter Island Heights, offering panoramic sea views from every room. It has an excellent user rating, location rating, and cleanliness rating. The house has 4 bedrooms and 4000 square feet of floor area. It has a private sandy beach, deep water dock, fitness center, tennis court, and concierge services.
10 1 review
Southold, NY
07/05 – 07/09
$4349/nighttotal: $17396 (4 )
Traditional-style Home With Private Pool, Sweeping Back Deck, Grand Lawn,...
4 4
apartment , Water Mill
This four-bedroom, three-bathroom Water Mill house rental is located just outside Bridgehampton, a short drive from the Parrish Art Museum and South Fork Natural History Museum. The 8-guest property boasts a private pool, expansive deck, well-equipped kitchen with stainless steel appliances, Wi-Fi, a washer/dryer, and ample parking, perfect for summer barbecues and relaxing after exploring the area.
Southold, NY
07/05 – 07/09
$821/nighttotal: $3284 (4 )
Charming 1-bedroom Apartment With Ac In Sag Harbor
1 4
apartment , Noyack
This Sag Harbor apartment is located less than 3 miles from downtown Sag Harbor and Bridgehampton, providing convenient access to The Hamptons Beaches, Cooper's Beach, the Sag Harbor Whaling and Historical Museum, and Bay Street Theatre. This 950 square feet rental offers a private entrance, a living room with a sectional sofa that converts to a king-sized bed, air conditioning, parking, and allows pets, accommodating up to 4 guests.
9.1 249 reviews
Southold, NY
07/05 – 07/09
$685/nighttotal: $2740 (4 )
The Cliffside Resort Condominiums
1 4
apartment , Greenport
This Greenport apartment is located just a short drive from downtown Greenport and the Hortons Point Lighthouse, offering easy access to the area's attractions. The apartment is highly rated for its cleanliness, location, and overall experience. The two-bedroom apartment spans 550 square feet and provides a comfortable space for your stay. Guests can enjoy amenities like a swimming pool, a private beach, and a terrace, as well as convenient features like a kitchen, air conditioning, and free Wi-Fi.
Neighborhoods and points of interest in Southold, NY
Search Vacation Rentals with Swimming Pool in Southold, NY
Enhance your coastal getaway with a Southold, NY vacation rental featuring a pool.
8.6 7 reviews
Southold, NY
07/05 – 07/09
$2921/nighttotal: $11684 (4 )
Beautiful Contemporary Water Mill Home Centrally Located With Private Pool
5 4
apartment , Water Mill
This Water Mill vacation home is located 2.1 miles from the Hamptons Beaches and within 6 miles of attractions like the Elizabeth A. Morton National Wildlife Refuge, Noyac Golf Club, Parrish Art Museum, and Duck Walk Vineyards. This six-bedroom, four-bathroom house sleeps twelve guests and boasts a private pool, hot tub, fenced yard, game room, and fully equipped kitchen, perfect for family getaways or group vacations.
Southold, NY
07/05 – 07/09
$21451/nighttotal: $85804 (4 )
Villa Kimaal - Luxury With Pool
5 4
house , Noyack
Villa Kimaal, a luxury 5-bedroom estate in Sag Harbor, is situated 1.7 miles from Havens Beach and 16 miles from Montauk Point Lighthouse. This 5,010-square-foot house boasts a private pool, sauna, spa, and bar, accommodating up to 15 guests and offering amenities including free Wi-Fi, parking, and room service.
Top-Rated Oceanfront Vacation Rentals in Southold, NY
These seaside vacation rentals in Southold, NY provide an excellent base for exploring the coast. Browse top local properties and plan your beach-town trip.
Southold, NY
07/05 – 07/09
$1566/nighttotal: $6264 (4 )
Historic Over-the-water 3-bedroom Loft Apartment
3 4
apartment , Mattituck
Southold, NY
07/05 – 07/09
$1765/nighttotal: $7060 (4 )
Newly Renovated Sag Harbor Beach House With Pool
2 4
apartment , Noyack
Southold, NY
07/05 – 07/09
$2888/nighttotal: $11552 (4 )
Waterfront Tranquility Near Sag Harbor Village
4 4
apartment , Noyack
Browse Luxury Vacation Rentals in Southold, NY
Experience 5-star comfort in a luxury Southold, NY vacation rental designed with premium amenities throughout.
Southold, NY
07/05 – 07/09
$1005/nighttotal: $4020 (4 )
2-bedroom Cottage In Sag Harbor With Huge Backyard. Close To Everything!
2 4
cottage , Noyack
Choose the Right Vacation Rentals with a Steam Room in Southold, NY
Relax with an on-site sauna at these vacation rentals in Southold, NY, perfect for a steam session after a day by the water.
