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 705 per night from May 26 to May 27
SAR 705
SAR 900 total
includes taxes & fees
26 May - 27 May
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! (165 reviews)
"I was so pleasantly surprised! The furniture all seemed new, our room was spotless and we had a brand new kitchen and bath! There were chairs and a small patio to sit outside and we were right in a Marina. Very convenient to drive to Greenport and Orient Point. Southold is a very cute town and Greenport ..."
Reviewed on 20 May 2025
Residence Inn by Marriott New York Long Island East End
2012 Old Country Road, Riverhead, NY
The price is SAR 604 per night from May 26 to May 27
SAR 604
SAR 690 total
includes taxes & fees
26 May - 27 May
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 ...
9/10 Wonderful! (955 reviews)
"Love"
Reviewed on 7 May 2025
Water's Edge Resort & Spa
1525 Boston Post Road, Westbrook, CT
The price is SAR 859 per night from May 26 to May 27
SAR 859
SAR 1,052 total
includes taxes & fees
26 May - 27 May
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 ...
8.6/10 Excellent! (1,003 reviews)
"Beautiful location. Comfortable accommodations. Knowledgeable, helpful staff."
Reviewed on 17 May 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.
North Fork 7 Bedroom Farmhouse Escape
Southold
Stay at this vacation home in Southold. Enjoy free WiFi, a water park, and a garden. Popular attractions The Old Field Vineyards and Horton Point Park are located ...
Convenient location, multi bedroom
"We were in town for a wedding with small children in tow- the house was perfectly located for us to get to wedding events in under 10 minutes but do be aware that it’s on a busy road. The house is set back so there wasn’t too much traffic noise, especially with the window AC units going. You could ..."
Reviewed on 7 August 2022
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! (284 reviews)
"Mother’s Day weekend for a family of 4. From start to finish, the stay was amazing. The check-in was so simple. The room was exactly how the photos showed. It was clean and roomy. The beach is a very short walk away. Even though the pool was not officially open yet, it looked wonderful. We have already ..."
Reviewed on 12 May 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! (216 reviews)
"Beach access. Quiet but close to shopping and dining"
Reviewed on 21 May 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.
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.
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
- Horton Lane Beach
- Corey Creek Winery
- The Old Field Vineyards
- Horton Point Park
- Mattebella Vineyards
- Cooper's Beach
- Splish Splash Water Park
- The Hamptons Beaches
- 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
- Amagansett Beach
- Westbrook Town Beach
- The Jewish Center of the Hamptons