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 ￥35,989 per night from Oct 13 to Oct 14
￥35,989
￥44,831 total
Oct 13 - Oct 14
includes taxes & fees
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! (206 reviews)
Quiet Gem
"Lovely hotel in a beautiful, quiet area. Great view and service. Staff was so friendly and helpful."
Reviewed on Sep 19, 2025
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd, Old Saybrook, CT
The price is ￥11,902 per night from Oct 12 to Oct 13
￥11,902
￥13,687 total
Oct 12 - Oct 13
includes taxes & fees
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! (1,004 reviews)
"Property was a little dated, but very comfortable. The staff was terrific."
Reviewed on Sep 27, 2025
Quality Inn Old Saybrook - Westbrook
100 Essex Rd, Old Saybrook, CT
The price is ￥14,526 per night from Oct 13 to Oct 14
￥14,526
￥16,705 total
Oct 13 - Oct 14
includes taxes & fees
Book a stay at this business-friendly hotel in Old Saybrook. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
7.6/10 Good! (1,009 reviews)
"Clean, quiet, friendly staff."
Reviewed on Sep 23, 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.
Fabulous Waterfront Property in the Heart of Wine Country
Peconic
Book a stay at this family-friendly cottage in Southold. Enjoy free WiFi, a water park, and a garden. Popular attractions Goldsmith's Inlet Park and Sannino's ...
9.8/10 Exceptional! (171 reviews)
"Great place and beautiful scenery"
Reviewed on Aug 31, 2025
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! (295 reviews)
"Very nice & affordable"
Reviewed on Sep 2, 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! (240 reviews)
"Great view of the water and nice amenities with the beach and pool."
Reviewed on Sep 8, 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.
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.
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.
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.
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.
Horton Point Park
Explore the great outdoors at Horton Point Park, a lovely green space in Southold. Wander the beaches or discover the sunsets in this family-friendly area.
Things to do
Long Island Wine and Food Day Trip with Sommelier host from NYC
￥21,679
per adult
From Mattituck: North Fork Area Bike Tour with Food Tasting
￥20,361
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.
