Southold, NY
Travel Guide
Visit Southold
The Shoals Suites and Slips
61600 Main Rd Southold NY
$345 nightly
The price is $391 total per night from Sep 1 to Sep 2
$391 total
Sep 1 - Sep 2
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! (311 reviews)
"A pool if possible and television in bedrooms. Food truck every evening in summer months would be nice."
Reviewed on Aug 2, 2026
Vine & Sand
47100 New York 25 Southold NY
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! (20 reviews)
"The hosts were very friendly and welcoming. They were always available when we had questions or needed anything. We enjoyed the fresh pastries and fresh fruit the 1st morning. They were very accommodating and had breakfast out early when we had to leave extra early for our event our 1st day."
Reviewed on Jun 24, 2026
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundableReserve now, pay when you stay
$109 nightly
The price is $126 total per night from Aug 6 to Aug 7
$126 total
Aug 6 - Aug 7
Total with taxes and fees
Stay at this hotel in Old Saybrook. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8/10 Very Good! (1,000 reviews)
"Room was clean enough, but in dire need of updating. Poor lighting, heavy on wood details, the bathtub had a large crack right in the middle. Carpet felt like it needed a good professional cleaning. We weren't aware of any "amenities" the property offered, but we only stayed 1 night. Staff was ..."
Reviewed on Aug 4, 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.
Perfect Waterfront Family Vacation Home next to the best vineyards in NY!
Southold NY
Book a stay at this beach vacation home in Southold. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Croteaux Vineyards and Mattebella Vineyards ...
10/10 Exceptional! (41 reviews)
"We had the most wonderful stay at this property and knew from the moment we walked in that it was something special. The house has real charm and soul. You can tell it was put together with care and love, not just decorated to look nice in photos. Every detail felt intentional.The outdoor space was ..."
Reviewed on Jul 30, 2026
North Fork 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' ...
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! (280 reviews)
"Perfect. Stayed multiple tines"
Reviewed on Aug 4, 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.
Stay near popular Southold attractions
Things to do
Full Day Private Long Island Wine Tours from New York City
$189
per adult
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- Visit Montauk
- Visit Sagaponack
- Visit Riverhead
- Visit Water Mill
- Visit South Jamesport
- East Hampton Main Beach
- 67 Steps Beach
- Visit Mattituck
- Visit Hampton Bays
- Visit Laurel
- Visit North Fork
- Visit Greenport
- Visit Aquebogue
- Visit Noyack
- Visit Bridgehampton
- Visit Sag Harbor
- Visit Montclair Colony
- Shinnecock Nation Cultural Center and Museum
- Visit East Marion
- Visit Hamptons
- Visit Amagansett
- Where to stay in Southold
- Visit Cutchogue
- Visit Village of Southampton
- Cooper's Beach
- Visit Suffolk County
- Visit Shelter Island
- Visit East Hampton
- Visit Jamesport
- Visit Long Island
- Southold Vacations
- The Old Field Vineyards
- Visit Shelter Island Heights
- Visit Orient
- Visit Wainscott
- Visit Westhampton Beach
- Visit Southampton
- Sparkling Pointe
- Mattebella Vineyards
- Osprey's Dominion
- Sannino's Bella Vita Vineyard
- The Old Field Vineyards
- Horton Point Park
- Corey Creek Winery
- Splish Splash Water Park
- East Hampton Main Beach
- Hammonasset Beach State Park
- Cooper's Beach
- Wolffer Estates Vineyard
- Orient Point County Park
- Hither Hills State Park
- Tanger Outlet Center
- Essex Steam Train
- Rocky Neck State Park
- Shinnecock Hills Golf Course
- Clinton Crossing Premium Outlets
- Macari Vineyards
- Connecticut River
- Ponquogue Beach
- Pindar Vineyards
- Harvey's Beach
- Sag Harbor Marine Park
