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
$169 nightly
The price is $194 total per night from Jan 22 to Jan 23
$194 total
Jan 22 - Jan 23, 2026
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! (230 reviews)
Great stay, will definitely go again
Reviewed on Dec 20, 2025
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
$223 nightly
The price is $256 total per night from Jan 5 to Jan 6
$256 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
Book a stay at this beach resort in Westbrook. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
8.8/10 Excellent! (1,001 reviews)
Everything was wonderful. Staff was friendly, very clean,we enjoyed it.
Reviewed on Dec 20, 2025
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
$69 nightly
The price is $79 total per night from Dec 29 to Dec 30
$79 total
Dec 29 - Dec 30
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! (1,007 reviews)
Its okay, some of the furniture didn't look in good shape. Bed was good, bathrooms were neat and good. I loved the rustic wood table. Also its high time we have smart TVs now. They are dirt cheap.
Reviewed on Dec 21, 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.
Beautifully farmhouse
Southold NY
Book a stay at this family-friendly vacation home in Southold. Enjoy free WiFi, a water park, and a garden. Popular attractions Sparkling Pointe and The Old ...
10/10 Exceptional! (3 reviews)
We spent a few days to attend a family wedding. We were 7 and the house was extremely comfortable for all of us. The house is 2 floors and there is no bathroom upstairs so keep that in mind when assigning sleeping arrangements. We found a well stocked welcome basket and a bottle of wine which were ...
Reviewed on Sep 8, 2025
“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
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr
Westhampton Beach NY
Book a stay at this family-friendly vacation home in Westhampton Beach. Enjoy private pools, a garden, and laundry facilities. Popular attractions Westhampton ...
9.8/10 Exceptional! (188 reviews)
Great host, everything that we needed for our trip was available, ample room for the 9 of us.
Reviewed on Dec 7, 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.
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.
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.
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.
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.
Things to do
The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC
$179
per adult
76% of travellers recommend
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
- The Old Field Vineyards
- Sparkling Pointe
- Sannino's Bella Vita Vineyard
- Osprey's Dominion
- Horton Point Park
- Corey Creek Winery
- Mattebella Vineyards
- Cooper's Beach
- East Hampton Main Beach
- Hammonasset Beach State Park
- Splish Splash Water Park
- Wolffer Estates Vineyard
- Essex Steam Train
- Shinnecock Hills Golf Course
- Hither Hills State Park
- Tanger Outlet Center
- Westbrook Town Beach
- Connecticut River
- Orient Point County Park
- Raphael Winery
- Clinton Crossing Premium Outlets
- Rocky Neck State Park
- Macari Vineyards
- Kontokosta Winery
- 67 Steps Beach
- Shinnecock Nation Cultural Center and Museum
- Hole-in-the-Wall Beach
