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 SAR 635 per night from Mar 5 to Mar 6
SAR 635
SAR 725 total
includes taxes & fees
5 Mar - 6 Mar
Stay at this 3.5-star hotel in Southold. Enjoy free WiFi, free bicycles on site, and a business center. Our guests praise the helpful staff in our reviews. Popular ...
9.4/10 Exceptional! (149 reviews)
"I can’t say enough great things about this place. Absolutely wonderful !"
Reviewed on 4 January 2025
Water's Edge Resort & Spa
1525 Boston Post Road, Westbrook, CT
The price is SAR 638 per night from Mar 5 to Mar 6
SAR 638
SAR 798 total
includes taxes & fees
5 Mar - 6 Mar
Stay at this 3.5-star beach resort in Westbrook. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the property condition ...
8.6/10 Excellent! (1,004 reviews)
"I love this property! I stayed for one night and there was a comedian and a lot of activity in the hotel which made for a great night! My only complaint is the bed! It was probably the least comfortable bed I have ever slept in a hotel. I had a horrible night sleep as the mattress was terrible! The ..."
Reviewed on 15 February 2025
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd, Old Saybrook, CT
The price is SAR 259 per night from Feb 20 to Feb 21
SAR 259
SAR 298 total
includes taxes & fees
20 Feb - 21 Feb
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. ...
7.6/10 Good! (920 reviews)
"Perfect place for our short stay, super clean and comfortable!"
Reviewed on 17 February 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.
Windward Shores Ocean Resort
2062 Montauk Highway, PO Box 7031, Amagansett, NY
Stay at this 3-star beach aparthotel in Amagansett. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms ...
8.6/10 Excellent! (271 reviews)
"Beautiful location, clean property, and nice staff. Just hard to turn in to the parking lot but not much that the hotel can do for that. The private beach is stunning."
Reviewed on 9 February 2025
10 Bedroom Hampton House with a regulation size Pickleball
Hampton Bays
Book a stay at this family-friendly vacation home in Hampton Bays. Enjoy private pools, a water park, and a garden. Popular attractions Ponquogue Beach and Tiana ...
9.8/10 Exceptional! (15 reviews)
Fantastic house for group of friends!
"Had so much fun this weekend in Hampton Bays! House was perfect for a group of friends - many bedrooms, bathrooms, great pool with tons of outdoor games, and even the arcade room inside! So close to the beach, and a number of great restaurants. Highly recommend this house, and appreciate how helpful ..."
Reviewed on 28 August 2022
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr
Westhampton Beach
Book a stay at this family-friendly vacation home in Westhampton Beach. Enjoy private pools, a water park, and a garden. Popular attractions Westhampton Beach ...
9.8/10 Exceptional! (160 reviews)
Family get to
"We had a wonderful stay. The house was great and check in and check out were both easy. We definition would love to stay again."
Reviewed on 12 January 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.
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.
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.
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.