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
$157 nightly
The price is $180 total per night from Jan 25 to Jan 26
$180 total
Jan 25 - Jan 26
Total with taxes and fees
Stay at this hotel in Southold. Enjoy free WiFi, free bicycles on site, and a business center. Our guests praise the helpful staff in our reviews. Popular attractions ...
9.4/10 Exceptional! (236 reviews)
The streaming TV service was confusing
Reviewed on Jan 19, 2026
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
$79 nightly
The price is $91 total per night from Jan 25 to Jan 26
$91 total
Jan 25 - Jan 26
Total with taxes and 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! (1,001 reviews)
muy limpias
Reviewed on Jan 8, 2026
Sound View Greenport
58775 County Rd 48 Greenport NY
$151 nightly
The price is $173 total per night from Feb 9 to Feb 10
$173 total
Feb 9 - Feb 10
Total with taxes and fees
Book a stay at this 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! (607 reviews)
This is our fourth trip back to the Soundview Inn, and we are big fans! The atmosphere is simple, modern, with a laid-back vibe. The rooms are well appointed and are finished with an indoor/outdoor use in mind. The room can be chilly in the winter, but it’s easy to get cozy. The included breakfast ...
Reviewed on Jan 10, 2026
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.
“Paradise Found” - Walk to Private Beach & In-Ground Pool!
Southold NY
Book a stay at this family-friendly vacation home in Southold. Enjoy a garden, laundry facilities, and patios. Popular attractions Croteaux Vineyards and Custer ...
10/10 Exceptional! (7 reviews)
We had a great stay. We enjoyed cooking in the beautiful kitchen and spending time with family. We hope to visit again!
Reviewed on Dec 19, 2025
The SandPiper
Greenport, NY
Stay at this vacation home in Greenport. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Railroad Museum of Long Island and East End Seaport ...
9.6/10 Exceptional! (30 reviews)
Terrific service, clean, excellent location.
Reviewed on Jan 4, 2026
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Southampton NY
Book a stay at this family-friendly vacation home in Southampton. Enjoy free WiFi, private pools, and a garden. Popular attractions Southampton Golf Range and ...
9.8/10 Exceptional! (32 reviews)
The perfect spot for our niece’s wedding weekend.The property is spacious and well appointed. Close to everything but still feels private. Comfortable beds and sitting areas. The pool was amazing and a great spot to relax between wedding events. We had 7 adults stay there was plenty of room for everyone. ...
Reviewed on Sep 26, 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.
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.
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.
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.
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.
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.
Things to do
Long Island Wine Tour North Fork Sights, Bites & Flights Full-Day
$559
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.
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- Sparkling Pointe
- The Old Field Vineyards
- Mattebella Vineyards
- Corey Creek Winery
- Horton Point Park
- Visit Peconic
- Sannino's Bella Vita Vineyard
- Peconic Vacations
- Goldsmith's Inlet Park
- Raphael Winery
- Crescent Beach
- Lenz Winery
- Pindar Vineyards
- Sunset Beach
- Bedell Cellars
- Visit Shelter Island Heights
- Visit Greenport
- Railroad Museum of Long Island
- Visit Shelter Island
- 8 Hands Farm
- Sannino's Bella Vita Vineyard
- The Old Field Vineyards
- Sparkling Pointe
- Corey Creek Winery
- Osprey's Dominion
- Horton Point Park
- Mattebella Vineyards
- Cooper's Beach
- East Hampton Main Beach
- Hammonasset Beach State Park
- Splish Splash Water Park
- Wolffer Estates Vineyard
- Shinnecock Hills Golf Course
- Hither Hills State Park
- Essex Steam Train
- Tanger Outlet Center
- Connecticut River
- Raphael Winery
- Rocky Neck State Park
- Orient Point County Park
- The Jewish Center of the Hamptons
- Macari Vineyards
- Clinton Crossing Premium Outlets
- Sunset Beach
- Sag Harbor Marine Park
- Shinnecock Nation Cultural Center and Museum
- Westbrook Town Beach
