Southold, NY
Travel Guide
Visit Southold
The Shoals Suites and Slips
61600 Main Rd Southold NY
$177 nightly
The price is $199 total per night from Apr 9 to Apr 10
$199 total
Apr 9 - Apr 10
Total with taxes and fees
Stay at this hotel in Southold. Enjoy free WiFi, free bicycles on site, and a business center. Our guests praise the helpful staff in our reviews. Popular attractions ...
9.4/10 Exceptional! (250 reviews)
Clean, spacious and thoughtful room amenities. Close by to town and great restaurants.
Reviewed on Mar 23, 2026
Vine & Sand
47100 New York 25 Southold NY
$423 nightly
The price is $484 total per night from Apr 9 to Apr 10
$484 total
Apr 9 - Apr 10
Total with taxes and fees
Book a stay at this business-friendly B&B in Southold. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Mattebella Vineyards and Croteaux ...
9.8/10 Exceptional! (16 reviews)
Location was perfect for visiting the wineries… breakfast was to die for!
Reviewed on Mar 22, 2026
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
$246 nightly
The price is $282 total per night from Apr 6 to Apr 7
$282 total
Apr 6 - Apr 7
Total with taxes and fees
Book a stay at this beach resort in Westbrook. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
8.8/10 Excellent! (1,007 reviews)
The room was perfect, staff was excellent, parking was right next to my room. Best Breakfast Sausage ever.
Reviewed on Mar 24, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Windward Shores Ocean Resort
2062 Montauk Highway Amagansett NY
Book a stay at this beach aparthotel in Amagansett. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms ...
8.8/10 Excellent! (310 reviews)
When I went to the property it was not shoveled. A challenge to get to the room. I enjoyed the room with minor things that could change.
Reviewed on Mar 2, 2026
North Fork Cottages & RV Resort
690 Queen St Greenport NY
Stay at this cottage in Greenport. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Railroad Museum of Long Island and Greenport Farmers' ...
4BR Beach Cottage sits on private beach. Sleeps 12 with comfort, Outdoor grill
Westbrook CT
Book a stay at this beach cottage in Westbrook. Enjoy free WiFi, a beach locale, and laundry facilities. Popular attractions Westbrook Town Beach and Clinton ...
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Popular places to visit
Sparkling Pointe
You can enjoy a tasting or tour at Sparkling Pointe during your travels to Southold. Discover the sunsets and wineries in this family-friendly area.
Osprey's Dominion
You can enjoy a tasting or tour at Osprey's Dominion during your travels to Southold. Wander the beautiful beaches in this family-friendly area.
Sannino's Bella Vita Vineyard
You can enjoy a tasting or tour at Sannino's Bella Vita Vineyard during your travels to Southold. Wander the beaches or discover the sunsets in this family-friendly area.
Horton Lane Beach
Why not spend a lazy afternoon at Horton Lane Beach during your trip to Southold? Stroll along the beaches or discover the area's sunsets.
Croteaux Vineyards
You can enjoy a tasting or tour at Croteaux Vineyards during your travels to Southold. Wander the beautiful beaches in this family-friendly area.
Corey Creek Winery
You can enjoy a tasting or tour at Corey Creek Winery during your travels to Southold. Wander the beautiful beaches in this family-friendly area.
Things to do
Full Day Private Long Island Wine Tours from New York City
$189
per adult
Long Island Wine Tour North Fork Sights, Bites & Flights Full-Day
$559
per adult
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- Sparkling Pointe
- The Old Field Vineyards
- Mattebella Vineyards
- Corey Creek Winery
- Horton Point Park
- Visit Peconic
- Sannino's Bella Vita Vineyard
- Peconic Vacations
- Goldsmith's Inlet Park
- Raphael Winery
- Crescent Beach
- Lenz Winery
- Pindar Vineyards
- Sunset Beach
- Bedell Cellars
- Visit Shelter Island Heights
- Visit Greenport
- Railroad Museum of Long Island
- Visit Shelter Island
- 8 Hands Farm
- Osprey's Dominion
- Sannino's Bella Vita Vineyard
- Corey Creek Winery
- Sparkling Pointe
- Mattebella Vineyards
- The Old Field Vineyards
- Horton Point Park
- Cooper's Beach
- Splish Splash Water Park
- East Hampton Main Beach
- Hammonasset Beach State Park
- Shinnecock Hills Golf Course
- Wolffer Estates Vineyard
- Hither Hills State Park
- Essex Steam Train
- Tanger Outlet Center
- Raphael Winery
- Parrish Art Museum
- Rocky Neck State Park
- Shinnecock Nation Cultural Center and Museum
- Westbrook Town Beach
- The Jewish Center of the Hamptons
- Sag Harbor Marine Park
- Kontokosta Winery
- Sunset Beach
- Macari Vineyards
