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
$174 nightly
The price is $199 total per night from Jan 7 to Jan 8
$199 total
Jan 7 - Jan 8, 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! (227 reviews)
Great sta
Reviewed on Dec 8, 2025
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
$79 nightly
The price is $91 total per night from Dec 21 to Dec 22
$91 total
Dec 21 - Dec 22
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! (1,000 reviews)
A welcoming place with some nice touches.
Reviewed on Nov 30, 2025
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
$244 nightly
The price is $281 total per night from Dec 10 to Dec 11
$281 total
Dec 10 - Dec 11
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! (1,009 reviews)
Amazing customer service!!
Reviewed on Dec 4, 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.
“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)
Well-appointed home in a quiet neighborhood. The house felt clean and taken care of. The pool and deck area are really nice for lounging outside. Would definitely recommend to someone else or stay again.
Reviewed on Sep 7, 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! (187 reviews)
We had a truly wonderful stay in this house. We came with our four daughters, their partners, and their three little babies (the 3-month-old twins and our 1-month-old grandson) to celebrate Thanksgiving together.For a big, lively family like ours, this home was comfortable, welcoming, and perfectly ...
Reviewed on Nov 30, 2025
Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn
Madison CT
Stay at this apartment in Madison. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Hammonasset Beach State Park and Allis-Bushnell House ...
10/10 Exceptional! (36 reviews)
The place was adorable and spotless, the beds were super comfortable it was perfect and a minute from the beach! We will be back. Thanks for a great time!
Reviewed on Nov 9, 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
- Sannino's Bella Vita Vineyard
- Sparkling Pointe
- Osprey's Dominion
- Corey Creek Winery
- Horton Point Park
- Mattebella Vineyards
- Cooper's Beach
- Hammonasset Beach State Park
- Essex Steam Train
- East Hampton Main Beach
- Splish Splash Water Park
- Wolffer Estates Vineyard
- Shinnecock Hills Golf Course
- Hither Hills State Park
- Tanger Outlet Center
- Orient Point County Park
- Connecticut River
- Westbrook Town Beach
- Raphael Winery
- Clinton Crossing Premium Outlets
- 67 Steps Beach
- Jamesport Vineyards
- Macari Vineyards
- Rocky Neck State Park
- Guild Hall
- Kontokosta Winery
