5/5 - Excellent
Verified traveler
Head into Greenport for the brewery, Aldo’s for coffee, Crazy Beans, and the waterfront. Pindar vineyard was a great time and there is a nice family farm directly across the street.
Southold, NY
Travel Guide
Visit Southold
The Shoals Suites and Slips
61600 Main Rd, Southold, NY
The price is SAR 706 per night from Apr 16 to Apr 17
SAR 706
SAR 901 total
includes taxes & fees
16 Apr - 17 Apr
Stay at this 3.5-star hotel in Southold. Enjoy free WiFi, free bicycles on site, and a business center. Our guests praise the helpful staff in our reviews. Popular ...
9.4/10 Exceptional! (156 reviews)
"Fantastic. The room was very comfortable with a kitchen area and large bathroom. There are boat slips outside and a view of the water."
Reviewed on 14 April 2025
Water's Edge Resort & Spa
1525 Boston Post Road, Westbrook, CT
The price is SAR 739 per night from Apr 16 to Apr 17
SAR 739
SAR 915 total
includes taxes & fees
16 Apr - 17 Apr
Stay at this 3.5-star beach resort in Westbrook. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the property condition ...
8.6/10 Excellent! (1,003 reviews)
"Staff is always very receptive and cordial!"
Reviewed on 10 April 2025
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd, Old Saybrook, CT
The price is SAR 296 per night from Apr 16 to Apr 17
SAR 296
SAR 341 total
includes taxes & fees
16 Apr - 17 Apr
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. ...
7.6/10 Good! (943 reviews)
"the property was close to the ocean. very pet friendly and accommodated our needs well"
Reviewed on 12 April 2025
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 7 Bedroom Farmhouse Escape
Southold
Stay at this vacation home in Southold. Enjoy free WiFi, a water park, and a garden. Popular attractions The Old Field Vineyards and Horton Point Park are located ...
9.4/10 Exceptional! (3 reviews)
Convenient location, multi bedroom
"We were in town for a wedding with small children in tow- the house was perfectly located for us to get to wedding events in under 10 minutes but do be aware that it’s on a busy road. The house is set back so there wasn’t too much traffic noise, especially with the window AC units going. You could ..."
Reviewed on 7 August 2022
Windward Shores Ocean Resort
2062 Montauk Highway, PO Box 7031, Amagansett, NY
Stay at this 3-star beach aparthotel in Amagansett. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms ...
8.6/10 Excellent! (274 reviews)
"2nd loft bedroom/bath was especially nice"
Reviewed on 30 March 2025
Cliffside Resort Condominiums
61475 Route 48 (North Road), Greenport, NY
Stay at this 3-star beach aparthotel in Greenport. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Railroad Museum of Long Island and ...
8.8/10 Excellent! (207 reviews)
"Stove it’s not efficient and refrigerator blocked with the corner of wall"
Reviewed on 5 November 2024
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.
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.
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.
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.
The Old Field Vineyards
You can enjoy a tasting or tour at The Old Field Vineyards during your travels to Southold. Stroll along the beaches or discover the sunsets 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.
Reviews of Southold
4.4
Top Destination
3/5 - Okay
Verified traveler
Expensive
5/5 - Excellent
Verified traveler
I love Southold and all the areas on the Northfork side.
5/5 - Excellent
Verified traveler
Quiet, North Fork town.
3/5 - Okay
Louise
Lots of wineries to visit with excellent wines. Tastings can be a bit expensive. One vineyard charged $16 for 3 - 2 oz tastings. It would have been less expensive to just buy a glass or a bottle of wine. A glass of wine was $11 - $13.
4/5 - Good
Trish
Took a wonderful Jet Ski tour around Shelter Island (Peconic Water Sports), Spent a wonderful day in Greenport.
- Sparkling Pointe
- Sannino's Bella Vita Vineyard
- Osprey's Dominion
- Croteaux Vineyards
- Corey Creek Winery
- The Old Field Vineyards
- Horton Lane Beach
- Mattebella Vineyards
- Horton Point Park
- Cooper's Beach
- The Hamptons Beaches
- Splish Splash Water Park
- East Hampton Main Beach
- Hammonasset Beach State Park
- Wolffer Estates Vineyard
- Hither Hills State Park
- Essex Steam Train
- Tanger Outlet Center
- Orient Point County Park
- Rocky Neck State Park
- Connecticut River
- Sag Harbor Marine Park
- 67 Steps Beach
- Harvey's Beach
- Shinnecock Hills Golf Course
- Kontokosta Winery
- Amagansett Beach
- Clinton Crossing Premium Outlets
- Westbrook Town Beach
- The Jewish Center of the Hamptons
- Jamesport Vineyards
- Shinnecock Nation Cultural Center and Museum