Southold, NY

Travel Guide

Southold
Photo by Benny Goh
Photo by Benny Goh
Photo by 4 Star Traveler
Photo by 4 Star Traveler
The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 out of 5
61600 Main Rd, Southold, NY
The price is ₩345,481 per night from Oct 14 to Oct 15
₩345,481
₩430,373 total
Oct 14 - Oct 15
includes taxes & fees
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! (210 reviews)
"Great place, beautiful views! I’ll be back."

Reviewed on Oct 6, 2025

The Shoals Suites and Slips
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd, Old Saybrook, CT
The price is ₩114,262 per night from Oct 14 to Oct 15
₩114,262
₩131,408 total
Oct 14 - Oct 15
includes taxes & 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! (1,009 reviews)
"Staff was incredibly communicative, kind, and patient. Definitely recommend and we would stay again!"

Reviewed on Oct 11, 2025

Pier Blue Inn Old Saybrook - Essex
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

2.5 out of 5
100 Essex Rd, Old Saybrook, CT
The price is ₩133,377 per night from Nov 2 to Nov 3
₩133,377
₩153,384 total
Nov 2 - Nov 3
includes taxes & 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! (1,005 reviews)
"Overall, a nice hotel for a one day trip! :)"

Reviewed on Oct 5, 2025

Quality Inn Old Saybrook - Westbrook
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

Windward Shores Ocean Resort

3 out of 5
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! (296 reviews)
"The non ocean view rooms are fabulous. I’m sure the ocean side ones are great."

Reviewed on Sep 30, 2025

Windward Shores Ocean Resort
Cliffside Resort Condominiums

Cliffside Resort Condominiums

3 out of 5
61475 Route 48 (North Road), Greenport, NY
Stay at this 3-star 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! (241 reviews)
"Easy in and out. Safe parking. Everything was set up for you"

Reviewed on Sep 29, 2025

Cliffside Resort Condominiums
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

Reviews of Southold

4.4
Top Destination
5 - Excellent
13
5 - Excellent 62%
4 - Good
5
4 - Good 24%
3 - Okay
2
3 - Okay 10%
2 - Disappointing
0
2 - Disappointing 0%
1 - Terrible
1
1 - Terrible 5%

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.

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.