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 635 per night from Apr 1 to Apr 2
SAR 635
SAR 819 total
includes taxes & fees
1 Apr - 2 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! (151 reviews)
"Love love love this place ! Can’t say enough"
Reviewed on 22 February 2025
Water's Edge Resort & Spa
1525 Boston Post Road, Westbrook, CT
The price is SAR 638 per night from Mar 26 to Mar 27
SAR 638
SAR 798 total
includes taxes & fees
26 Mar - 27 Mar
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! (1,001 reviews)
"Lovely property .... The dinner was great . Room service was very convenient and fast . The spa was wonderful Justine was amazing with the massage I felt so relaxed after. Our pedicures the next day were equally amazing, my feet are so soft and clean my polish is neat. I will definitely be back for ..."
Reviewed on 10 March 2025
Hyatt Place Long Island East End
451 East Main Street, Riverhead, NY
The price is SAR 401 per night from Mar 20 to Mar 21
SAR 401
SAR 459 total
includes taxes & fees
20 Mar - 21 Mar
Stay at this 3-star business-friendly hotel in Riverhead. Enjoy free WiFi, free parking, and a marina. Our guests praise the breakfast and the helpful staff ...
9/10 Wonderful! (1,000 reviews)
Weekend getaway
"This hotel was top notch from top to bottom. Room was clean and our bed was very comfortable. Service was also excellent. A+++++"
Reviewed on 9 March 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! (275 reviews)
"Great cozy place"
Reviewed on 4 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.
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.
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.
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.
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
- The Old Field Vineyards
- Corey Creek Winery
- Croteaux Vineyards
- Horton Lane Beach
- Osprey's Dominion
- Mattebella Vineyards
- Horton Point Park
- The Hamptons Beaches
- Cooper's Beach
- Splish Splash Water Park
- East Hampton Main Beach
- Hammonasset Beach State Park
- Wolffer Estates Vineyard
- Long Island Aquarium and Exhibition Center
- Tanger Outlet Center
- Hither Hills State Park
- Essex Steam Train
- Orient Point County Park
- Connecticut River
- Rocky Neck State Park
- 67 Steps Beach
- Sag Harbor Marine Park
- Harvey's Beach
- Shinnecock Hills Golf Course
- Clinton Crossing Premium Outlets
- Kontokosta Winery
- The Jewish Center of the Hamptons
- Jamesport Vineyards
- Shinnecock Nation Cultural Center and Museum
- Macari Vineyards