Compare best Airbnb in Southold, NY from 100+ providers!

279 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
Southold, NY vacation rentals
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

Best Vacation rentals and Airbnb offers in Southold, NY

Best Southold, NY vacation rentals with a balcony

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.
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.
Waterfront Condo C-204 At The Cliffside Resort - Southold, NY
9.9 197 reviews

Waterfront Condo C-204 At The Cliffside Resort

apartment, Greenport
Water's Edge luxury suite is located in the Captain's Roost Building of The Cliffside Resort Condominiums in Greenport, New York, on the North Fork of Long Island, with panoramic waterfront views from the master bedroom, living room, and private covered deck. Rated excellent by users for its location, cleanliness, and amenities, this two-bedroom, two-bathroom apartment accommodates up to 6 guests in 700 square feet.
The apartment features a fully equipped kitchenette with a dishwasher, air conditioning, a DVD player, a folding laptop table, a sturdy step ladder, a small vacuum, and cleaning supplies. Guests have access to a seasonal pool and coin-operated washer and dryer in the basement, as well as a private beach just yards away.

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.

Cozy Greenport Village Cottage - Southold, NY
10 9 reviews

Cozy Greenport Village Cottage

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.
Greenport Beachfront Home | Private Beach & Sunset - Southold, NY
No reviews

Greenport Beachfront Home | Private Beach & Sunset

apartment, Southold
This Southold beachfront rental offers direct private access to the North Fork of Long Island's tranquil waters, ideal for swimming, fishing, paddleboarding, and kayaking. This family-friendly 4-bedroom, 2-bathroom house accommodates up to 9 guests and features a full kitchen, air conditioning, a garden, fitness center, parking, an expansive dual-sided deck with a firepit and dining area, and a dedicated outdoor BBQ for enjoying unobstructed sunset views.
Shelter Island Retreat With Pool, Home Theater, Close To Beach & Pet Friendly - Southold, NY
10 21 reviews

Shelter Island Retreat With Pool, Home Theater, Close To Beach & Pet Friendly

apartment, Shelter Island Heights
This family-friendly vacation home is located in Shelter Island Heights, just a short distance from Crescent Beach, Sunset Beach, and Shelter Island Country Club. This rental has received excellent reviews from previous guests.
The house has 3 bedrooms and 3 bathrooms, comfortably accommodating up to 7 guests. The home features a private pool, barbecue grills, a garden, a fireplace, and a game room for entertainment.
Fabulous Waterfront Property In The Heart Of Wine Country - Southold, NY
10 193 reviews

Fabulous Waterfront Property In The Heart Of Wine Country

cottage, Southold
This charming Southold cottage is located just a short walk from the Long Island Sound and its sandy beach, offering a peaceful escape in a picturesque setting. It's also close to wineries, restaurants, and local attractions, making it a great base for exploring the North Fork. Guests consistently rate this vacation rental excellent.
The cottage has three bedrooms, one bathroom, and sleeps five comfortably. It features a fully equipped kitchen, air conditioning, a private garden, a spa, and parking, ensuring a comfortable and enjoyable stay.

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 North Fork Hideaway - Southold, NY
10 5 reviews

Cozy North Fork Hideaway

apartment, Cutchogue
This 1-bedroom country condo in Cutchogue offers a peaceful setting, just a short distance from Nassau Point beaches, award-winning wineries, farm stands, restaurants, and North Fork villages. This accommodation includes a fully equipped kitchen, air conditioning, internet, and parking, with a capacity for 2 guests seeking modern comforts in a cozy atmosphere.
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.
Waterfront Greenport Getaway - Southold, NY
9.7 23 reviews

Waterfront Greenport Getaway

apartment, Greenport
This Greenport waterfront condo overlooks the Long Island Sound on the North Fork, offering easy access to the town's shops and restaurants.
The two-bedroom, two-bathroom unit sleeps six and includes a kitchen, air conditioning, parking, a swimming pool, and a private balcony with stunning Long Island Sound views; enjoy nearby boating and fishing.
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.

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.
Greenport Getaway At Cliffside Condos - Southold, NY
9.8 33 reviews

Greenport Getaway At Cliffside Condos

apartment, Greenport
This cliffside condo in Greenport offers direct access to a private beach and is located within 1 mile of Greenport's shops, restaurants, and vineyards.
This 2-bedroom, 2-bathroom condo accommodates up to 6 guests with a queen bed, two twin beds, and a pullout sofa, featuring a kitchen with a fridge, microwave, and dishwasher, air conditioning, a seasonal swimming pool, garden, and BBQ facilities.
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.
Nofo  Escape Relax-swim-enjoy. Bachelorettes-weddings-family Vacation - Southold, NY
9.8 31 reviews

Nofo Escape Relax-swim-enjoy. Bachelorettes-weddings-family Vacation

apartment, Greenport
This Greenport vacation rental is located a short walk from the town center, beach, vineyard, and restaurants, with proximity to Camera Obscura and Greenport Carousel.
This spacious 6-bedroom, 6-bathroom house offers 2500 square feet of living space for up to 12 guests, featuring a pool, spa, garden, and parking, and is ideal for fishing, boating, and exploring the East End Seaport Maritime Museum.

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.

North Fork Sound Front Home With Pool - Southold, NY
9.8 44 reviews

North Fork Sound Front Home With Pool

apartment, Greenport
Wine Country Home - Southold, NY
10 46 reviews

Wine Country Home

apartment, Cutchogue
Beachfront Greenport Villa - Southold, NY
9.8 13 reviews

Beachfront Greenport Villa

apartment, Southold
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

Browse Luxury Vacation Rentals in Southold, NY

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

The Cliffside Resort Condominiums - Southold, NY
9.2 223 reviews

The Cliffside Resort Condominiums

apartment, Greenport

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.

Charming North Fork Escape - Southold, NY
10 13 reviews

Charming North Fork Escape

apartment, Southold
©2026 cozycozy.com