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
$177 nightly
The price is $203 total per night from Dec 13 to Dec 14
$203 total
Dec 13 - Dec 14
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! (221 reviews)
This was a stunning place to stay in all respects. The large room was wonderrful. Thank you!
Reviewed on Nov 8, 2025
Quality Inn Old Saybrook - Westbrook
100 Essex Rd Old Saybrook CT
$101 nightly
The price is $116 total per night from Nov 30 to Dec 1
$116 total
Nov 30 - Dec 1
Total with taxes and fees
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 helpful ...
7.6/10 Good! (1,007 reviews)
Staff was kind. Easy, comfortable stay.
Reviewed on Nov 19, 2025
Sound View Greenport
58775 County Rd 48 Greenport NY
$199 nightly
The price is $227 total per night from Dec 18 to Dec 19
$227 total
Dec 18 - Dec 19
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! (593 reviews)
Amazing views and comfy bed and room. No sound privacy between the rooms at all! I guess they o relooked sound insulation in an otherwise gorgeous renovation of a roadside motel.
Reviewed on Nov 19, 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)
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
Cliffside Resort Condominiums
61475 Route 48 (North Road) Greenport NY
Book a stay at this 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! (248 reviews)
The unit was cute and well-appointed. I would recommend a new refrigerator in the unit, as the freezer door was broken.
Reviewed on Nov 12, 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.
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.
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.
Things to do
The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC
$179
per adult
76% of travellers recommend
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
- Corey Creek Winery
- Horton Point Park
- Mattebella Vineyards
- Osprey's Dominion
- Cooper's Beach
- Essex Steam Train
- East Hampton Main Beach
- Hammonasset Beach State Park
- Splish Splash Water Park
- Wolffer Estates Vineyard
- Shinnecock Hills Golf Course
- Orient Point County Park
- Hither Hills State Park
- Tanger Outlet Center
- Raphael Winery
- Connecticut River
- Clinton Crossing Premium Outlets
- 67 Steps Beach
- Guild Hall
- Jamesport Vineyards
- Kontokosta Winery
- Westbrook Town Beach
