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Southold, NY vacation rentals
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Best Vacation rentals and Airbnb offers in Southold, NY

Best Southold, NY vacation rentals with a balcony

New Victorian Gem In Greenport - Southold, NY
10 14 reviews

New Victorian Gem In Greenport

apartment, Greenport
This newly renovated Victorian vacation home in Greenport offers a historic stay within a short walk to the village center, providing convenient access to restaurants, shopping, and the East End Seaport Maritime Museum.
This 5-bedroom, 4-bathroom house accommodates up to 12 guests with features like a kitchen including a fridge, microwave, and dishwasher, air conditioning, a swimming pool, terrace, garden, and parking, with proximity to The Hamptons Beaches and Orient Beach State Park.
Spacious And Modern North Fork Home Close To Multiple Wineries, Perfect For... - Southold, NY
10 7 reviews

Spacious And Modern North Fork Home Close To Multiple Wineries, Perfect For...

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.
4br/3.5ba: Southold, Fire Pit, Close To Town/beach - Southold, NY
9.9 24 reviews

4br/3.5ba: Southold, Fire Pit, Close To Town/beach

apartment, Southold
This Southold vacation home is located just 0.3 miles from The Old Field Vineyards and within a 3-mile radius of Sparkling Pointe and Mattebella Vineyards, making it an ideal choice for wine enthusiasts. The property has received excellent ratings for location, cleanliness, and overall user experience.
This 3,500 square foot home comfortably accommodates up to 10 guests. Enjoy a fully equipped kitchen, a washing machine, 4 bathrooms, a fireplace, a balcony, a barbecue grill, and a Smart TV for entertainment.
Aqua Vista - Southold, NY
9.9 757 reviews

Aqua Vista

apartment, Greenport
This Greenport apartment is located in the center of Greenport Village, just steps away from restaurants, shops, and the Shelter Island Ferry. It has excellent user, location, and cleanliness ratings. This two-bedroom rental comfortably sleeps six guests. It features a fully equipped kitchen, a private balcony, and a garden.
The apartment is air-conditioned, has free internet access, and allows pets, making it a perfect choice for families and groups.

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.

Northfork Townhouse Walk To All - Southold, NY
10 7 reviews

Northfork Townhouse Walk To All

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.
Walk To Town, Marina Views, Greenport Village - Southold, NY
9.8 79 reviews

Walk To Town, Marina Views, Greenport Village

apartment, Greenport
This charming vacation rental is conveniently located in Greenport, just a short walk from the hospital, the farmers' market, and popular attractions like the Greenport Carousel and Camera Obscura. The house has received excellent ratings for its location, cleanliness, and overall experience.
This 2-bedroom, 2-bathroom home comfortably accommodates up to 6 guests. Amenities include a fully equipped kitchen, air conditioning, a jacuzzi, a terrace, a garden, parking, and free WiFi, providing everything you need for a relaxing and enjoyable stay.
Beachfront Greenport Villa - Southold, NY
9.8 13 reviews

Beachfront Greenport Villa

apartment, Southold
This beachfront home is located in Greenport, directly on the Long Island Sound, within walking distance of restaurants and bars in the Soundview area and a short bike ride from North Fork wineries, breweries, farms, and the town center. This 3-bedroom, 3-bathroom house can accommodate up to 8 guests and offers amenities such as a fully equipped kitchen, air conditioning, a garden, a spa, and parking for 3 cars.
Country Beach Home! - Southold, NY
9.9 20 reviews

Country Beach Home!

apartment, Southold
This Southold home, ideally situated in the heart of the North Fork, offers easy access to local wineries, farms, and shops, all within minutes of the property.
The 4-bedroom, 3-bathroom house sleeps 10 guests and features a gourmet chef's kitchen, a spacious open floor plan with a fireplace, a tranquil patio with a Weber BBQ, and extensive beach gear for nearby excursions.

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?

    The Cliffside Resort Condominiums, Sound Front Condominium and Waterfront Condo C-204 At The Cliffside Resort are the most popular Airbnb and vacation rentals in Southold, NY among travelers.

  • 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.

Popular destinations

Best Southold, NY vacation rentals with parking

Cozy  Cottage On The Great Pond Near Beach. - Southold, NY
9.8 202 reviews

Cozy Cottage On The Great Pond Near Beach.

apartment, Southold
This Southold waterfront cottage, near Long Island Sound and Southold's wineries, offers easy access to hiking trails and farm stands.
The two-bedroom, one-bathroom home sleeps four and features a fully equipped kitchen, air conditioning, on-site watercraft rentals (kayak, canoe, paddle boat), and a screened porch.
Lovely Cottage In The Heart Of Long Island Wine Country - Southold, NY
9.8 32 reviews

Lovely Cottage In The Heart Of Long Island Wine Country

cottage, Southold
This waterfront cottage in Southold offers stunning views and a private garden with barbecue grills for outdoor entertainment. It's conveniently located near Horton Lane Beach, Sparkling Pointe, and Horton Point Park.
With an excellent user rating, this 2-bedroom, 2-bathroom cottage features a cozy fireplace, a fully equipped kitchen with a microwave, coffee/tea maker, and dishwasher, and a TV for entertainment. It also has a terrace/balcony, a garden, parking, and allows pets.
The Greenport Bungalow - Southold, NY
9.9 295 reviews

The Greenport Bungalow

apartment, Greenport
This modern Greenport bungalow is located just an 8-minute walk from the beach, the town center, the Shelter Island Ferry, and the Long Island Rail Road train station.
This three-bedroom, two-bathroom home comfortably sleeps five guests and boasts a spacious backyard, a fully equipped kitchen, and access to the entire home and wifi.
Bright, Southold Studio Apt Near Beach & Town - Southold, NY
9.9 157 reviews

Bright, Southold Studio Apt Near Beach & Town

apartment, Southold
This Southold apartment is just a 5-minute walk from the bay beach, farmstands, a supermarket, and the historic village center, making it a convenient base for exploring the charming North Fork town. It consistently receives excellent ratings for location, cleanliness, and overall experience.
The studio apartment comfortably sleeps two guests and features a modern, light-filled interior with a full bathroom and a small kitchenette. Enjoy the fresh air on the private patio, complete with WiFi, and get to know Ethel and Carrie, the friendly chickens who roam the property.

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.

Traditional Southold Home, Private Heated Saltwater Pool, Perfect For Families - Southold, NY
10 1 review

Traditional Southold Home, Private Heated Saltwater Pool, Perfect For Families

apartment, Southold
This Southold apartment is located on a private, peaceful block, providing convenient access to wineries, restaurants, shops, and nearby beaches on the North Fork.
This 2000 sq ft rental accommodates up to 8 guests with 5 bedrooms and 3 bathrooms, featuring a private, heated saltwater pool, a wood-burning fire pit, and a laptop-friendly workspace.
Spacious North Fork Home In Greenport, Heated Pool, Perfect For Families - Southold, NY
10 4 reviews

Spacious North Fork Home In Greenport, Heated Pool, Perfect For Families

apartment, Southold
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.
North Fork Resort - Southold, NY
9.6 1 review

North Fork Resort

resort, Greenport
Vacation resort listing with an excellent rating of 96% based on 1 reviews. You will be in Greenport.
Services and facilities: a kitchen, a swimming pool and a barbecue. Take advantage of the Free Parking with this resort.
New Construction Greenport Pool House - 3 Blocks From Town - Southold, NY
10 4 reviews

New Construction Greenport Pool House - 3 Blocks From Town

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.

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.

Greenport Walk To Beach & Vineyard From This Brand New Home - Southold, NY
10 10 reviews

Greenport Walk To Beach & Vineyard From This Brand New Home

apartment, Southold
Adorable Cottage - Southold, NY
9.9 116 reviews

Adorable Cottage

apartment, Southold
Beachfront Greenport Villa - Southold, NY
10 1 review

Beachfront Greenport Villa

house, Southold
Luxury By The Sea - Southold, NY
10 12 reviews

Luxury By The Sea

apartment, Southold

Browse Luxury Vacation Rentals in Southold, NY

Experience 5-star comfort in a luxury Southold, NY vacation rental designed with premium amenities throughout.

Cozy North Fork Hideaway - Southold, NY
10 5 reviews

Cozy North Fork Hideaway

apartment, Cutchogue

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.

The Cliffside Resort Condominiums - Southold, NY
9.2 223 reviews

The Cliffside Resort Condominiums

apartment, Greenport
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