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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

Brand New Build! Greenport Gem W/ Yard & Patio - Southold, NY
No reviews

Brand New Build! Greenport Gem W/ Yard & Patio

apartment, Greenport
This Greenport apartment is located near the beach, within walking distance of the Greenport Carousel and Camera Obscura.
This 1750 sq ft rental offers 3 bedrooms, 4 bathrooms, and can accommodate up to 6 guests, featuring a fully equipped kitchen, air conditioning, a garden with a barbecue area, and Wi-Fi.
Southold Waterfront With Boat Dock, Boat Ramp, Hot Tub & Beaches - Southold, NY
10 185 reviews

Southold Waterfront With Boat Dock, Boat Ramp, Hot Tub & Beaches

apartment, Southold
This waterfront vacation home in Southold is a short walk from a beautiful bathing beach and is situated on a quiet private road with minimal traffic. Guests consistently rate this rental as excellent.
The home features four bedrooms and three bathrooms, comfortably accommodating up to eight guests. Amenities include a private floating dock, kayaks, canoes, a stand-up paddleboard, a paddleboat, a year-round outdoor hot tub, a waterside fire pit, two grills, and a spacious garden.
Peconic Sound Beach Cottage Walk To Sound - Southold, NY
9.0 2 reviews

Peconic Sound Beach Cottage Walk To Sound

house, Peconic
This Peconic vacation home is located just 19 miles from Splish Splash and a short distance from Goldsmith's Inlet Park, offering easy access to popular attractions and a peaceful escape. The house features three bedrooms, two living rooms, and two bathrooms, accommodating up to seven guests in its 7,050 square feet of space. The house offers a fully equipped kitchen, satellite TV, a fitness center, a terrace, and a backyard with stunning sea views for a comfortable and enjoyable stay.
Meadowood Manor By Rove Travel - 6br Outdoor Spaces - Southold, NY
9.2 38 reviews

Meadowood Manor By Rove Travel - 6br Outdoor Spaces

house, Noyack
Meadowood Manor, a Sag Harbor house rental in Noyack, is conveniently located near Foster Memorial Beach (1.7 miles) and offers easy access to other Long Island attractions like Montauk Point Lighthouse (20-27 miles away).
This 3400-square-foot home boasts a fully equipped kitchen, private patio, swimming pool, jacuzzi, and free Wi-Fi, perfect for a relaxing Noyack getaway.

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
9.4 8 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.
Greenport Village View - Walk Downtown 2br/1ba - Southold, NY
9.9 272 reviews

Greenport Village View - Walk Downtown 2br/1ba

apartment, Greenport
This Greenport apartment is conveniently located in the heart of Greenport Village, within walking distance of restaurants, shops, the Greenport Brewery, and Kontakasta Winery. The apartment has received excellent ratings for location, cleanliness, and user experience.
The apartment offers two bedrooms, one bathroom, and can accommodate up to four guests. Guests can enjoy amenities such as a fully equipped kitchen, a washer and dryer, cable TV, wireless internet, beach chairs, and parking.
Luxury By The Sea - Southold, NY
10 12 reviews

Luxury By The Sea

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.
1820 Whaling Captain's Home - A Walk To A Coffee Or Cocktail! - Southold, NY
10 63 reviews

1820 Whaling Captain's Home - A Walk To A Coffee Or Cocktail!

apartment, Greenport
This Greenport vacation home is a short walk from Eastern Long Island Hospital, Greenport Farmers' Market, and Stony Brook Eastern Long Island Hospital, making it convenient for exploring the town and surrounding area. It's rated excellent by previous guests.
The 1700 square foot home can comfortably accommodate up to 5 guests in its 3 bedrooms and 2 bathrooms. It offers a range of amenities, including a fully equipped kitchen, a private yard, a fireplace, and a DVD player, 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

The Cliffside Resort Condominiums - Southold, NY
9.2 219 reviews

The Cliffside Resort Condominiums

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.
Walk To Town, Greenport Village 1st Floor Apt - Southold, NY
9.9 82 reviews

Walk To Town, Greenport Village 1st Floor Apt

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.
North Fork Classic Walk To Town - Southold, NY
9.6 11 reviews

North Fork Classic Walk To Town

house, Southold
This Southold house rental is centrally located, a short walk from Southold's town center and a five-minute drive from area beaches.
The three-bedroom, one-bathroom home sleeps six, features a fully equipped kitchen with dishwasher, air conditioning, a private deck with gas grill, ample parking, and Wi-Fi; nearby restaurants include North Fork Table & Inn and Southold Social.
Private Waterfront Access + Hot Tub + Scenic Yard - Southold, NY
10 45 reviews

Private Waterfront Access + Hot Tub + Scenic Yard

apartment, Southold
This Southold house rental, permit #1184, is located near Goose Creek, a five-minute walk from Croteaux Vineyards, Custer Observatory, and Sophie's, with easy access to Greenport and Southold village.
The spacious three-bedroom, two-and-a-half-bathroom home sleeps six, features a kitchen with a microwave and dishwasher, air conditioning, a garden, parking, internet access, and two bikes for guest use.

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.

Newly Renovated, Stylish Peconic Retreat With Private Pool, Lush Grounds,... - Southold, NY
10 5 reviews

Newly Renovated, Stylish Peconic Retreat With Private Pool, Lush Grounds,...

apartment, Southold
This Southold rental is conveniently located near Sannino's Bella Vita Vineyard (a 10-minute walk) and Raphael's Winery (a 2-minute drive), offering easy access to local wineries.
The four-bedroom, 2.5-bathroom apartment sleeps eight, features a fully equipped kitchen, in-unit laundry, a swimming pool, and a terrace, plus nearby beaches and attractions like the Long Island Railroad Museum and Horton Point Park.
Historic Luxury Seaside  Getaway - Southold, NY
9.9 116 reviews

Historic Luxury Seaside Getaway

apartment, New Suffolk
This New Suffolk apartment is located just steps from the beach and within walking distance of two restaurants. It has consistently received excellent ratings for its cleanliness, location, and overall experience.
The 3600 square foot home has six bedrooms and four bathrooms, comfortably accommodating up to 16 guests. Amenities include a heated swimming pool, two patios, a yard, kayaks, bicycles, and a chef's kitchen ideal for hosting large gatherings.
Beautiful Hampton Retreat- Sag Harbor Tennis And Pool On 2 Private Acres - Southold, NY
10 8 reviews

Beautiful Hampton Retreat- Sag Harbor Tennis And Pool On 2 Private Acres

apartment, Noyack
This luxurious 4-bedroom, 3-bathroom rental home is situated in Sag Harbor, near the Noyac Golf Club and offers easy access to other Hamptons towns, beaches, and attractions such as Channing Daughters Winery and Harbes Family Farm.
The 2-acre property boasts a heated pool, hot tub, outdoor barrel sauna, tennis and basketball courts, a recently renovated interior with high ceilings and an open living area, accommodating up to 8 guests and providing a tranquil escape.
Nassau Point, North Fork Home W/ Pool - Southold, NY
9.9 87 reviews

Nassau Point, North Fork Home W/ Pool

apartment, Cutchogue
This Cutchogue rental is minutes from a local sandy beach and Long Island's 38 vineyards.
The four-bedroom, three-bathroom home sleeps eight, features a spacious open-plan kitchen, dining, and living area opening onto a deck and private pool, and includes amenities such as Wi-Fi, a dishwasher, and air conditioning.

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.

Luxury North Fork Beachfront Escape Near Greenport - Southold, NY
10 51 reviews

Luxury North Fork Beachfront Escape Near Greenport

apartment, Southold
Waterfront Condo C-204 At The Cliffside Resort - Southold, NY
9.9 200 reviews

Waterfront Condo C-204 At The Cliffside Resort

apartment, Greenport
Aqua Vista - Southold, NY
9.9 761 reviews

Aqua Vista

apartment, Greenport
Lovely 1st Floor Of Farmhouse, Wineries/downtown - Southold, NY
9.9 65 reviews

Lovely 1st Floor Of Farmhouse, Wineries/downtown

apartment, Greenport

Browse Luxury Vacation Rentals in Southold, NY

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

Traditional Southold Family Home - Southold, NY
10 1 review

Traditional Southold Family Home

apartment, Southold

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.

Steps From The Water! Southold Northfork Retreat - Southold, NY
9.9 34 reviews

Steps From The Water! Southold Northfork Retreat

apartment, Southold
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