Southold, NY
Travel Guide
Visit Southold
The Shoals Suites and Slips
61600 Main Rd Southold NY
$238 nightly
The price is $268 total per night from May 28 to May 29
$268 total
May 28 - May 29
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! (268 reviews)
Very helpful staff. Room was very roomy (no pun intented) and appeared to be recently upgraded. Chit provided for continental breakfast at a local coffee shop that was very good. Definitely recommend.
Reviewed on May 5, 2026
Vine & Sand
47100 New York 25 Southold NY
$351 nightly
The price is $401 total per night from May 11 to May 12
$401 total
May 11 - May 12
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
Sound View Greenport
58775 County Rd 48 Greenport NY
$326 nightly
The price is $373 total per night from May 10 to May 11
$373 total
May 10 - May 11
Total with taxes and fees
Book a stay at this beach hotel in Greenport. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
8.6/10 Excellent! (645 reviews)
Beautiful place to stay on a special getaway
Reviewed on May 7, 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.
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' ...
8.8/10 Excellent! (13 reviews)
Great stay & great staff!
Reviewed on May 7, 2026
Cliffside Resort Condominiums
61475 Route 48 (North Road) Greenport NY
Book a stay at this beach aparthotel in Greenport. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Railroad Museum of Long Island and ...
9/10 Wonderful! (252 reviews)
This is my third time at the Cliffside, and as always it was a lovely space that was great value for money. The only reason I didn’t give it five stars was that the heat was wildly inconsistent: in the small bedroom it was very hot, and the kitchen/living room, cool, and in the master bedroom, frigid. ...
Reviewed on Apr 21, 2026
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! (312 reviews)
We always stay at the Windward Shores when we go to Montauk. It is a beautiful, clean and comfortable place, and the price is great!
Reviewed on May 6, 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.
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.
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.
Mattebella Vineyards
You can enjoy a tasting or tour at Mattebella Vineyards during your travels to Southold. Wander the beautiful beaches in this family-friendly area.
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
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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
- Mattebella Vineyards
- Sparkling Pointe
- Corey Creek Winery
- The Old Field Vineyards
- Sannino's Bella Vita Vineyard
- Horton Point Park
- Cooper's Beach
- Splish Splash Water Park
- Hammonasset Beach State Park
- East Hampton Main Beach
- Shinnecock Hills Golf Course
- Wolffer Estates Vineyard
- Essex Steam Train
- Orient Point County Park
- Hither Hills State Park
- Tanger Outlet Center
- Rocky Neck State Park
- Macari Vineyards
- Parrish Art Museum
- Shinnecock Nation Cultural Center and Museum
- Sag Harbor Marine Park
- The Jewish Center of the Hamptons
- Westbrook Town Beach
- Hole-in-the-Wall Beach
- Sunset Beach
