5/5 - Excellent
Verified traveler
Oct 15, 2019Head 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
The Shoals Suites and Slips
61600 Main Rd, Southold, NY
The price is $295 per night from May 9 to May 10
$295
$362 total
includes taxes & fees
May 9 - May 10
Stay at this hotel in Southold. Enjoy free breakfast, free WiFi, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. ...
9.4/10 Exceptional! (75 reviews)
"Would go back in a heartbeat. The staff were so friendly and the rooms are gorgeous. Honestly it’s a best kept secret and I’m so glad we found it!"
Reviewed on Apr 29, 2024
Quality Inn Old Saybrook - Westbrook
100 Essex Rd, Old Saybrook, CT
The price is $89 per night from May 9 to May 10
$89
$102 total
includes taxes & fees
May 9 - May 10
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 pool ...
7.4/10 Good! (954 reviews)
"convenient good breakfast"
Reviewed on Apr 25, 2024
Hilton Garden Inn Riverhead
2038 Old Country Rd, Riverhead, NY
The price is $128 per night from May 28 to May 29
$128
$146 total
includes taxes & fees
May 28 - May 29
Stay at this hotel in Riverhead. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. ...
8.4/10 Very Good! (978 reviews)
"Highly recommended!"
Reviewed on May 6, 2024
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 property ...
8.6/10 Excellent! (233 reviews)
"Everything was just as described!"
Reviewed on Apr 28, 2024
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. Our guests praise the clean rooms in our reviews. Popular ...
8.8/10 Excellent! (180 reviews)
"Always a very nice time staying at this property. The sunset on the beach was amazing. Convenient to all area restaurants, wineries, breweries and Matchbook Distilling."
Reviewed on Mar 17, 2024
North Fork Escape Near Wineries, Beaches And Hamptons
Riverhead
Stay at this vacation home in Riverhead. Enjoy free WiFi, private pools, and a water park. Our guests praise the clean rooms in our reviews. Popular attractions ...
9.2/10 Wonderful! (18 reviews)
Family getaway
"Lovely quaint home. Very clean and spacious. Perfect for a family getaway . Highly recommend."
Reviewed on Nov 25, 2023
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.
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.
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 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.
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.
Things to do
Long Island Full Day Wine and Food Tasting Vineyard Tour from NYC
$159
Per adult
Private Hamptons Tour with Outlet Center Shopping
$1,199
Per adult
Reviews of Southold
4.4
Top Destination
3/5 - Okay
Verified traveler
Sep 9, 2019Expensive
5/5 - Excellent
Verified traveler
Aug 16, 2019I love Southold and all the areas on the Northfork side.
5/5 - Excellent
Verified traveler
Jul 23, 2019Quiet, North Fork town.
3/5 - Okay
Louise
May 13, 2019Lots 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
Sep 17, 2018Took a wonderful Jet Ski tour around Shelter Island (Peconic Water Sports), Spent a wonderful day in Greenport.
- Sparkling Pointe
- Sannino's Bella Vita Vineyard
- Corey Creek Winery
- Mattebella Vineyards
- The Old Field Vineyards
- Osprey's Dominion
- Horton Point Park
- Splish Splash Water Park
- Hammonasset Beach State Park
- Cooper's Beach
- East Hampton Main Beach
- Wolffer Estates Vineyard
- Hither Hills State Park
- Rocky Neck State Park
- Essex Steam Train
- Tanger Outlet Center
- Orient Point County Park
- Clinton Crossing Premium Outlets
- Connecticut River
- 67 Steps Beach
- Harvey's Beach
- Sag Harbor Marine Park
- Stony Creek - Thimble Islands Historic District
- Orient Beach State Park
- Kontokosta Winery
- Shinnecock Hills Golf Course
- Sunset Beach
- Hole-in-the-Wall Beach