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
The price is AED 572 per night from Apr 2 to Apr 3
AED 572
AED 745 total
2 Apr - 3 Apr
includes taxes & 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! (243 reviews)
Clean and spacious room
Reviewed on 19 February 2026
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
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. ...
8/10 Very Good! (1,001 reviews)
Not fancy but very cute. Clean. Super nice staff. Cozy, delicious Indian restaurant right next door.
Reviewed on 1 March 2026
Sound View Greenport
58775 County Rd 48 Greenport NY
The price is AED 562 per night from Mar 18 to Mar 19
AED 562
AED 747 total
18 Mar - 19 Mar
includes taxes & 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! (618 reviews)
Staff was over the top helpful, nice!!!! If you needed help or anything they were right on it for you Thank you do very much for making a sad trip for a loved ones memorial into something grateful!!
Reviewed on 1 March 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.
Aqua Vista
Greenport, NY
Stay at this vacation home in Greenport. Enjoy free WiFi, laundry facilities, and balconies. Popular attractions Railroad Museum of Long Island and East End ...
9.8/10 Exceptional! (25 reviews)
Love the place stairs are a bit tricky if you have trouble with normal ones
Reviewed on 15 February 2026
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
Hampton Bays NY
Book a stay at this beach vacation home in Hampton Bays. Enjoy a beach locale, a garden, and laundry facilities. Popular attractions Meschutt Beach and Good ...
4BR Beach Cottage sits on private beach. Sleeps 12 with comfort, Outdoor grill
Westbrook CT
Book a stay at this beach cottage in Westbrook. Enjoy free WiFi, a beach locale, and laundry facilities. Popular attractions Westbrook Town Beach and Clinton ...
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.
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.
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.
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.
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.
