Southold, NY
Travel Guide





Visit Southold

The Shoals Suites and Slips
61600 Main Rd Southold NY
$397 nightly
The price is $450 total per night from Jul 26 to Jul 27
$450 total
Jul 26 - Jul 27
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! (292 reviews)
"Had an amazing stay here during the off season with our newborn. The room was clean and grounds were beautifully maintained. Can’t wait to come back here this summer to see the property in full action."
Reviewed on Jul 8, 2026

Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
$96 nightly
The price is $111 total per night from Jul 12 to Jul 13
$111 total
Jul 12 - Jul 13
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! (1,013 reviews)
"The room was hot, and AC barely worked."
Reviewed on Jul 10, 2026

Sound View Greenport
58775 County Rd 48 Greenport NY
$552 nightly
The price is $630 total per night from Aug 3 to Aug 4
$630 total
Aug 3 - Aug 4
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 ...
8.4/10 Very Good! (664 reviews)
"The staff was helpful and nice. The exterior of the property was fine and the landscaping pretty. However the room was awful - not particularly clean, a noisy, wall ac plugged in next to the bed, felt like a renovated motel room. Sorry not worth $700/ night."
Reviewed on Jul 8, 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 Custer Institute and Observatory and ...
10/10 Exceptional! (39 reviews)
"Lovely home in Southold! Comfortable beds, adequate 2 baths… third was a great outdoor shower. Kitchen had everything we needed. Very nice furnishings and linens. Outdoor spaces were fantastic!"
Reviewed on Jun 22, 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' ...
9.4/10 Exceptional! (30 reviews)
"Overall the stay was pleasant. The cottages are well maintained. This property is still developing so there was active construction. It listed some amenities that were not yet available and some that were only available through a weekend stay which we did not have with a Sunday-Tuesday booking. I ..."
Reviewed on Jul 8, 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! (269 reviews)
"Comfortable and clean, and the beach location is amazing. The sunset was spectacular. We will definitely come back again!"
Reviewed on Jul 11, 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 Cutchogue
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- Southold Vacations
- The Old Field Vineyards
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- Sparkling Pointe
- Sannino's Bella Vita Vineyard
- Osprey's Dominion
- The Old Field Vineyards
- Corey Creek Winery
- Mattebella Vineyards
- Horton Point Park
- Splish Splash Water Park
- Cooper's Beach
- Shinnecock Hills Golf Course
- East Hampton Main Beach
- Hammonasset Beach State Park
- Wolffer Estates Vineyard
- Hither Hills State Park
- Essex Steam Train
- Tanger Outlet Center
- Rocky Neck State Park
- Orient Point County Park
- Harvey's Beach
- Clinton Crossing Premium Outlets
- Macari Vineyards
- Connecticut River
- Parrish Art Museum
- Ponquogue Beach
- Westbrook Town Beach
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