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 ₩393,544 per night from Jul 27 to Jul 28
₩393,544
₩483,458 total
Jul 27 - Jul 28
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! (173 reviews)
"Amazing"
Reviewed on Jun 15, 2025
Vine & Sand
47100 New York 25, Southold, NY
Stay at this 3-star business-friendly B&B in Southold. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Croteaux Vineyards and Corey Creek ...
10/10 Exceptional! (7 reviews)
"We enjoyed an amazing wine weekend at Vine and Sand. Beautiful home and relaxing, enjoyable stay. Great location for visiting vineyards as well as the villages of Southold and Greenport."
Reviewed on Feb 17, 2025
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd, Old Saybrook, CT
The price is ₩102,075 per night from Jun 29 to Jun 30
₩102,075
₩117,386 total
Jun 29 - Jun 30
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. ...
7.6/10 Good! (981 reviews)
"This is a great place to stay with an outstanding location in Old Saybrook right on RT 1. Great breakfast cafe right across the street."
Reviewed on Jun 24, 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.
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! (285 reviews)
"Easy checking in and out Easy access few steps to beach from first floor unit"
Reviewed on Jun 14, 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! (222 reviews)
"Quiet"
Reviewed on Jun 23, 2025
Canoe Place Waterfront Residences
239 E Montauk Hwy, Hampton Bays, NY
Stay at this 4-star spa condo in Hampton Bays. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Cooper's Beach and Meschutt Beach are ...
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.
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.
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.
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.
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.