Southold holiday homes
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Find the best place to stay - Southold
Sea Breeze Paradise: Beachfront & Panoramic Views
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens 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 some of the reasons to come on holiday to 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 looking for attractions to see during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Southold a fun place to get away to. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:
- Raphael Winery (2.7 mi / 4.4 km)
- Pindar Vineyards (3 mi / 4.9 km)
- Bedell Cellars (3.3 mi / 5.3 km)
- Peconic Bay Winery (4.2 mi / 6.8 km)
- Kontokosta Winery (4.7 mi / 7.6 km)
- Macari Vineyards (9.2 mi / 14.7 km)
Exploring the natural landscape of Southold
Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Southold is a great spot to appreciate mother nature. These are a few of the area's noteworthy sights, all within 30 miles (48.2 km) of the city centre:
- 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)
Transport to and around Southold
The nearest airport is in East Hampton, NY (HTO), located 11.8 mi (18.9 km) from the city centre. If you're unable to find a flight that fits your schedule, you can also fly into Westhampton, NY (FOK-Francis S. Gabreski), which is 19 mi (30.6 km) away.
If you prefer train travel, the main station is Southold Station.