Southold vacation rentals
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Gorgeous private Hamptons house with pool and volleyball court
Top rated rentals - Southold
Photo gallery for Southold cottage with Private Beach Rights ~ Walk to Kayak & Paddle Board
Cute cottage for local trip
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
- More for lessMore space, more privacy, more amenities — more value
Explore the waterfront setting in Southold
The area's wineries and monuments are just a few of the reasons to vacation in Southold. Renowned for its island views, beaches and gardens, this city welcomes all visitors. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.
Activities and attractions in and around Southold
Are you hoping to discover things to do in the city? Venture out of your vacation home and experience everything that makes Southold a fun spot to vacation. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:
- Raphael Winery (2.7 mi / 4.4 km)
- Pindar Vineyards (3 mi / 4.9 km)
- Bedell Cellars (3.3 mi / 5.3 km)
- Greenport Carousel (4.2 mi / 6.8 km)
- Peconic Bay Winery (4.2 mi / 6.8 km)
- Kontokosta Winery (4.7 mi / 7.6 km)
Exploring the natural landscape of Southold
Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your vacation in Southold. Here are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city center:
- Crescent Beach (2.9 mi / 4.7 km)
- Sunset Beach (3.2 mi / 5.2 km)
- 67 Steps Beach (4.8 mi / 7.8 km)
- Sag Harbor Marine Park (8.2 mi / 13.1 km)
- Orient Beach State Park (9.5 mi / 15.2 km)
- The Hamptons Beaches (11.6 mi / 18.6 km)
Transportation to and around Southold
The nearest airport is in East Hampton, NY (HTO), located 11.8 mi (18.9 km) from the city center. If you can't find a flight that's convenient for your trip, you could also fly into Westhampton, NY (FOK-Francis S. Gabreski), which is 19 mi (30.6 km) away.
If you'd prefer to travel by train, you can make your way to Southold Station.