Book Hotels in Southold, NY
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Top Southold hotels

The Shoals Suites and Slips
61600 Main Rd, Southold, NY
$255 nightly
The price is $288 total per night from Nov 2 to Nov 3
$288 total
Nov 2 - Nov 3
Total with taxes and fees
A restaurant and a bar/lounge are featured at this hotel. A business center, a coffee shop, and a communal living room are also on offer.
"Nice! Good location too"
Reviewed on Sep 26, 2025

Saybrook Point Resort & Marina
2 Bridge St, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
$331 nightly
The price is $380 total per night from Nov 2 to Nov 3
$380 total
Nov 2 - Nov 3
Total with taxes and fees
A full-service spa, a marina, and 2 outdoor pools are all featured at this smoke-free hotel. Traveling on business? Take advantage of the free WiFi in public ...
"My husband used the spa and said it was excellent. The housekeeping staff was generally good - -forgot some tasks a couple of times. Front of the house staff excellent. Special shoutout to Jack!! Very surprised that there was no inroom safe. Bathroom needs a remodel -needs taller counters…as well ..."
Reviewed on Sep 26, 2025

The Bentley Hotel Southampton
161 Hills Station Rd, Southampton, NY
Fully refundableReserve now, pay when you stay
$148 nightly
The price is $169 total per night from Oct 5 to Oct 6
$169 total
Oct 5 - Oct 6
Total with taxes and fees
A seasonal outdoor pool, free self parking, and laundry facilities are featured at this hotel. If you want to take your pet along, this pet-friendly property ...
"Staff and management were very helpful with the room change request. Property was ideal with large rooms and comfort for a quick stay in the hamptons. Great value!"
Reviewed on Sep 26, 2025

Water's Edge Resort & Spa
1525 Boston Post Road, Westbrook, CT
Fully refundableReserve now, pay when you stay
$219 nightly
The price is $252 total per night from Oct 26 to Oct 27
$252 total
Oct 26 - Oct 27
Total with taxes and fees
This smoke-free resort features a private beach, a full-service spa, and 3 restaurants. Relax with beach cabanas and sun loungers, and cool off with a drink ...
"Beautiful grounds and quiet private beach"
Reviewed on Sep 27, 2025

Sound View Greenport
58775 County Rd 48, Greenport, NY
$291 nightly
The price is $332 total per night from Oct 27 to Oct 28
$332 total
Oct 27 - Oct 28
Total with taxes and fees
A private beach and a restaurant are featured at this smoke-free hotel. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Unwind with ...
"Clean and beautiful view"
Reviewed on Sep 16, 2025

Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
$82 nightly
The price is $95 total per night from Oct 22 to Oct 23
$95 total
Oct 22 - Oct 23
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers ...
"Only issue....the refrigerator makes an annoying sound which is amlpified wearing hearing aids"
Reviewed on Sep 30, 2025

Quality Inn Old Saybrook - Westbrook
100 Essex Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
$94 nightly
The price is $108 total per night from Nov 2 to Nov 3
$108 total
Nov 2 - Nov 3
Total with taxes and fees
This hotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. ...
"Liked having and using pool. didn't realize there would be a swimming lesson going on at same time. As this was a quick stop over on our way to Bar Harbor, it fit our needs. Since the room was on the street side it was a bit noisy even with fan running all the time. The room was clean and comfortable ..."
Reviewed on Sep 28, 2025

Greenview Inn Riverhead
1433 W Main St, Riverhead, NY
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $123 total per night from Oct 16 to Oct 17
$123 total
Oct 16 - Oct 17
Total with taxes and fees
Free self parking is available and the motel's front desk is staffed around-the-clock. WiFi in public areas is free. A garden is also provided.
"Serene environment, very neat and clean."
Reviewed on Sep 24, 2025

The Atlantic Hotel
1655 County Road 39, Southampton, NY
$138 nightly
The price is $158 total per night from Nov 2 to Nov 3
$158 total
Nov 2 - Nov 3
Total with taxes and fees
This hotel's 2 outdoor tennis courts and outdoor pool are among the featured amenities. Guests will appreciate free perks like free self parking and WiFi in ...
"Really more of a motel not a hotel. Room was basic but adequate and clean. Close to Southampton. They were fully booked on one of the weekend days of our stay so rate that night was high for this type of lodging."
Reviewed on Sep 30, 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.
Frequently asked questions
Recent Southold hotel reviews by fellow wanderers

Pier Blue Inn Old Saybrook - Essex
5 out of 5
Posted 2 days ago
Travelocity Verified Review
"Only issue....the refrigerator makes an annoying sound which is amlpified wearing hearing aids"
A verified traveler stayed at Pier Blue Inn Old Saybrook - Essex
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