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 SAR 845 per night from Sep 21 to Sep 22
SAR 845
SAR 1,059 total
21 Sep - 22 Sep
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! (204 reviews)
"Ahhh what a chill spot! Everything is brand new, classic and beautiful. Complimentary bikes, breakfast and outdoor showers! The view of the water, the fire pit, the hammock set the stage for a relaxing getaway! We will be back!"
Reviewed on 8 September 2025
Sound View Greenport
58775 County Rd 48, Greenport, NY
Fully refundableReserve now, pay when you stay
The price is SAR 1,049 per night from Oct 15 to Oct 16
SAR 1,049
SAR 1,382 total
15 Oct - 16 Oct
includes taxes & fees
Stay at this 4-star beach hotel in Greenport. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
8.4/10 Very Good! (566 reviews)
Wonderful but the bathroom is too small
"We loved our stay. It’s like a motel turned eco friendly resort. We had an upper corner room, which afforded us unobstructed views and privacy. The bed was so comfortable and the room was spacious—except for the bathroom. The bathroom needs vanity space! While the charm of this place is partly due ..."
Reviewed on 7 September 2025
The Atlantic Hotel
1655 County Road 39, Southampton, NY
Book a stay at this business-friendly hotel in Southampton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
7/10 Good! (928 reviews)
"Very nice staff and great location"
Reviewed on 7 September 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! (170 reviews)
"Great place and beautiful scenery"
Reviewed on 31 August 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! (293 reviews)
"Very nice & affordable"
Reviewed on 2 September 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 8 September 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.
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.
- Sannino's Bella Vita Vineyard
- Croteaux Vineyards
- Sparkling Pointe
- Osprey's Dominion
- Corey Creek Winery
- Horton Point Park
- The Old Field Vineyards
- Horton Lane Beach
- Mattebella Vineyards
- Splish Splash Water Park
- The Hamptons Beaches
- Cooper's Beach
- Hammonasset Beach State Park
- East Hampton Main Beach
- Essex Steam Train
- Wolffer Estates Vineyard
- Orient Point County Park
- Hither Hills State Park
- Tanger Outlet Center
- Kontokosta Winery
- Connecticut River
- 67 Steps Beach
- Shinnecock Hills Golf Course
- Harvey's Beach
- Clinton Crossing Premium Outlets
- Sag Harbor Marine Park
- Rocky Neck State Park
- Sunset Beach
- Macari Vineyards
- Pindar Vineyards
