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Southold, NY vacation rentals
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Southold, NY Vacation rentals: no available offers. Here are other great options for your stay!

Beach Block Hideaway - Southold, NY
9.9 34 reviews

Beach Block Hideaway

apartment, Greenport
This newly-renovated two-bedroom condo offers an unbeatable location directly on the same block as the Greenport Village beach and a short walk to the shops and dining of Greenport Village.
This pet-friendly unit accommodates up to 8 guests with king-size beds in both bedrooms, features keyless entry, and provides easy access to local wineries and North Fork weddings.
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.
Beautifully Decorated Sound Front Resort Condo - Southold, NY
9.9 39 reviews

Beautifully Decorated Sound Front Resort Condo

apartment, Greenport
This Suffolk County condo, part of the "Beautifully Decorated Sound Front Resort Condo" offer, is located in Greenport, New York, offering easy access to local attractions, though precise distances aren't specified.
The two-bedroom, two-bathroom unit sleeps six and includes amenities such as a swimming pool, garden, and parking; further details on square footage and specific resort features are unavailable.
Greenport Walk To Beach & Vineyard! Brand New Home - Southold, NY
10 78 reviews

Greenport Walk To Beach & Vineyard! Brand New Home

apartment, Southold
This Southold apartment is just a short walk from the beach and a winery, offering easy access to the North Fork's best attractions. It's also a quick drive from the Halyard Restaurant and other wineries, restaurants, and shops. The apartment consistently receives excellent ratings for location, cleanliness, and user experience.
This comfortable home features three bedrooms and two bathrooms, comfortably accommodating up to six guests. Enjoy amenities like air conditioning, a private garden, parking, a fully equipped kitchen, and a Weber grill for outdoor dining.

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.

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