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
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 ...
Residence Inn by Marriott New York Long Island East End
2012 Old Country Road, Riverhead, NY
Stay at this 3-star business-friendly hotel in Riverhead. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the property ...
Water's Edge Resort & Spa
1525 Boston Post Road, Westbrook, CT
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 ...
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.
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 ...
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 ...
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.
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.
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.
Things to do
Half-Day Private Long Island Wine Tour Experience
$280
per adult
Long Island North Fork Sights Bites & Flights, Half-Day Tour: AM
$399
per adult
Long Island North Fork Sights, Bites & Flights: Full-Day Tour
$595
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.
- Sparkling Pointe
- Osprey's Dominion
- Sannino's Bella Vita Vineyard
- Croteaux Vineyards
- Corey Creek Winery
- The Old Field Vineyards
- Horton Point Park
- Mattebella Vineyards
- Custer Institute and Observatory
- McCabe's Beach
- Cooper's Beach
- Splish Splash Water Park
- East Hampton Main Beach
- Hammonasset Beach State Park
- Wolffer Estates Vineyard
- Hither Hills State Park
- Essex Steam Train
- Rocky Neck State Park
- Orient Point County Park
- Sag Harbor Marine Park
- Connecticut River
- 67 Steps Beach
- Tanger Outlet Center
- Shinnecock Hills Golf Course
- Harvey's Beach
- Kontokosta Winery
- Jamesport Vineyards
- Westbrook Town Beach
- The Jewish Center of the Hamptons