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 ￥26,450 per night from Feb 8 to Feb 9
￥26,450
￥30,219 total
Feb 8 - Feb 9
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! (234 reviews)
The room was much larger than expected, very clean. Perfect location, Melissa at the front desk was very helpful
Reviewed on Jan 1, 2026
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
The price is ￥35,884 per night from Jan 11 to Jan 12
￥35,884
￥43,971 total
Jan 11 - Jan 12
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! (1,005 reviews)
Great place!
Reviewed on Dec 31, 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! (1,002 reviews)
Parking was very convenient, and the property is pet-friendly with a nice grassy area in the back for pets to relieve themselves. The room was clean and staff were friendly, although queen size bed felt like twin xl but overall, a pleasant and hassle-free stay.
Reviewed on Dec 31, 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.
“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 Dec 19, 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 Dec 24, 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.
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.
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.
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.
Things to do
The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC
￥28,026
per adult
76% of travellers recommend
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.
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