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
$149 nightly
The price is $171 total per night from Mar 22 to Mar 23
$171 total
Mar 22 - Mar 23
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! (244 reviews)
Very friendly
Reviewed on Mar 6, 2026
Vine & Sand
47100 New York 25 Southold NY
$307 nightly
The price is $351 total per night from Mar 22 to Mar 23
$351 total
Mar 22 - Mar 23
Total with taxes and fees
Book a stay at this business-friendly B&B in Southold. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Mattebella Vineyards and Croteaux ...
9.6/10 Exceptional! (15 reviews)
Vine + Sand was wonderful. The hosts were so friendly and it was close to many wineries.
Reviewed on Jan 19, 2026
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
$184 nightly
The price is $212 total per night from Apr 1 to Apr 2
$212 total
Apr 1 - Apr 2
Total with taxes and 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! (1,004 reviews)
This was my first time at Water’s Edge and will definitely not be my last. Our stay was wonderful. Becky at the front desk was
Reviewed on Mar 7, 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.
North Fork Cottages & RV 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' ...
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
Hampton Bays NY
Book a stay at this beach vacation home in Hampton Bays. Enjoy a beach locale, a garden, and laundry facilities. Popular attractions Meschutt Beach and Good ...
4BR Beach Cottage sits on private beach. Sleeps 12 with comfort, Outdoor grill
Westbrook CT
Book a stay at this beach cottage in Westbrook. Enjoy free WiFi, a beach locale, and laundry facilities. Popular attractions Westbrook Town Beach and Clinton ...
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.
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.
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.
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.
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.
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.
Things to do
Full Day Private Long Island Wine Tours from New York City
$189
per adult
Long Island Wine Tour North Fork Sights, Bites & Flights Full-Day
$559
per adult
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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- Sparkling Pointe
- The Old Field Vineyards
- Mattebella Vineyards
- Corey Creek Winery
- Horton Point Park
- Visit Peconic
- Sannino's Bella Vita Vineyard
- Peconic Vacations
- Goldsmith's Inlet Park
- Raphael Winery
- Crescent Beach
- Lenz Winery
- Pindar Vineyards
- Sunset Beach
- Bedell Cellars
- Visit Shelter Island Heights
- Visit Greenport
- Railroad Museum of Long Island
- Visit Shelter Island
- 8 Hands Farm
- Sannino's Bella Vita Vineyard
- Osprey's Dominion
- Corey Creek Winery
- The Old Field Vineyards
- Mattebella Vineyards
- Sparkling Pointe
- Horton Point Park
- Cooper's Beach
- Splish Splash Water Park
- Hammonasset Beach State Park
- East Hampton Main Beach
- Shinnecock Hills Golf Course
- Wolffer Estates Vineyard
- Hither Hills State Park
- Essex Steam Train
- Connecticut River
- Tanger Outlet Center
- Parrish Art Museum
- Raphael Winery
- Shinnecock Nation Cultural Center and Museum
- The Jewish Center of the Hamptons
- Orient Point County Park
- Jamesport Vineyards
- Rocky Neck State Park
- Westbrook Town Beach
- Guild Hall
