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 AED 566 per night from Jan 26 to Jan 27
AED 566
AED 646 total
26 Jan - 27 Jan
includes taxes & 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! (235 reviews)
Friendly staff, area was cleaned
Reviewed on 12 January 2026
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
The price is AED 841 per night from Jan 15 to Jan 16
AED 841
AED 1,031 total
15 Jan - 16 Jan
includes taxes & fees
Book a stay at this beach resort in Westbrook. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
8.8/10 Excellent! (1,007 reviews)
Great place!
Reviewed on 31 December 2025
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
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. ...
7.8/10 Good! (1,003 reviews)
muy limpias
Reviewed on 8 January 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.
“Paradise Found” - Walk to Private Beach & In-Ground Pool!
Southold NY
Book a stay at this family-friendly vacation home in Southold. Enjoy a garden, laundry facilities, and patios. Popular attractions Croteaux Vineyards and Custer ...
10/10 Exceptional! (7 reviews)
We had a great stay. We enjoyed cooking in the beautiful kitchen and spending time with family. We hope to visit again!
Reviewed on 19 December 2025
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr
Westhampton Beach NY
Book a stay at this family-friendly vacation home in Westhampton Beach. Enjoy private pools, a garden, and laundry facilities. Popular attractions Westhampton ...
9.8/10 Exceptional! (189 reviews)
Was the perfect place for our family with 3 adults and 3 teenage who each had their own rooms. Very convenient location and the host gave us lots of suggestions. Definitely recommend anyone looking for a place to stay to stay here. We plan on going back next year!
Reviewed on 24 December 2025
4-bedroom beach house minutes from Hamptons
Calverton NY
Stay at this vacation home in Calverton. Enjoy a garden, laundry facilities, and balconies. Popular attractions Wildwood State Park and Baiting Hallow Golf Club ...
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.
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.
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.
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.
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.
- Horton Lane Beach
- Sannino's Bella Vita Vineyard
- The Old Field Vineyards
- Croteaux Vineyards
- Corey Creek Winery
- Osprey's Dominion
- Sparkling Pointe
- Horton Point Park
- Mattebella Vineyards
- The Hamptons Beaches
- Cooper's Beach
- East Hampton Main Beach
- Hammonasset Beach State Park
- Splish Splash Water Park
- Wolffer Estates Vineyard
- Hither Hills State Park
- Shinnecock Hills Golf Course
- Essex Steam Train
- Tanger Outlet Center
- Connecticut River
- Clinton Crossing Premium Outlets
- Orient Point County Park
- Rocky Neck State Park
- Raphael Winery
- Westbrook Town Beach
- Macari Vineyards
- 67 Steps Beach
- Sag Harbor Marine Park
- Sunset Beach
- Shinnecock Nation Cultural Center and Museum
