Book Hotels in Southold, NY
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Top Southold hotels

Vine & Sand
47100 New York 25 Southold NY
$351 nightly
The price is $401 total per night from Apr 22 to Apr 23
$401 total
Apr 22 - Apr 23
Total with taxes and fees
A seasonal outdoor pool is featured at this bed & breakfast, along with free self parking. Guests will appreciate free perks like buffet breakfast and WiFi in ...
Location was perfect for visiting the wineries… breakfast was to die for!
Reviewed on Mar 22, 2026

The Bentley Hotel Southampton
161 Hills Station Rd Southampton NY
Fully refundableReserve now, pay when you stay
$140 nightly
The price is $160 total per night from Apr 27 to Apr 28
$160 total
Apr 27 - Apr 28
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 ...
Fridge and microwave, coffe
Reviewed on Apr 19, 2026

The Shoals Suites and Slips
61600 Main Rd Southold NY
$194 nightly
The price is $218 total per night from May 5 to May 6
$218 total
May 5 - May 6
Total with taxes and fees
This hotel features a bar/lounge, a coffee shop, and a communal living room. A business center, a picnic area, and express check-out are also on offer.
The room was spacious. I’m very clean. I was very impressed. Location easy to get in and out of highly recommend.
Reviewed on Apr 14, 2026

Sag Harbor Inn
45 West Water Street Sag Harbor NY
$225 nightly
The price is $257 total per night from Apr 22 to Apr 23
$257 total
Apr 22 - Apr 23
Total with taxes and fees
An outdoor pool is featured at this hotel, along with free self parking. Enjoy the free continental breakfast each morning. A fireplace in the lobby and luggage ...
Lovely stay at Sag Harbor Inn. The room was great with a fantastic view of the water. The staff were super friendly and helpful.
Reviewed on Apr 20, 2026

Hyatt Place Long Island East End
451 East Main Street Riverhead NY
Fully refundableReserve now, pay when you stay
$144 nightly
The price is $165 total per night from May 6 to May 7
$165 total
May 6 - May 7
Total with taxes and fees
A marina, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center and ...
Good breakfast clean room
Reviewed on Apr 16, 2026

Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
$294 nightly
The price is $338 total per night from Apr 22 to Apr 23
$338 total
Apr 22 - Apr 23
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 ...
pleasant visit staff very friendly
Reviewed on Apr 16, 2026

The Harbor Front Inn
209 Front St Greenport NY
$223 nightly
The price is $255 total per night from Apr 26 to Apr 27
$255 total
Apr 26 - Apr 27
Total with taxes and fees
This hotel features a 24-hour gym and a seasonal outdoor pool. Business travelers can take advantage of the free WiFi in public areas. Enjoy the free continental ...
Really nice property!
Reviewed on Apr 16, 2026

Sound View Greenport
58775 County Rd 48 Greenport NY
$244 nightly
The price is $279 total per night from May 4 to May 5
$279 total
May 4 - May 5
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 ...
View is stunning but rooms feel dated. Bathroom is extremely tiny and terrace had uncomfortable furniture.
Reviewed on Apr 18, 2026

Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundable
$91 nightly
The price is $104 total per night from Apr 27 to Apr 28
$104 total
Apr 27 - Apr 28
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 ...
Was clean unique didnt expect to see the rooms so nice for the price and the rooms are unique in its own way
Reviewed on Apr 19, 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.
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Recent Southold hotel reviews by fellow wanderers

Quality Inn Old Saybrook - Westbrook
3 out of 5
Posted 12 hours ago
Travelocity Verified Review
"I was first placed in a dirty room but they were very quick and efficient to move me which was great b/c I don’t like first floor rooms. In my second room on 2nd floor the window lock was broken so I couldn’t lock it. Uncomfortable but being in 2nd floor helped. Clock in the room nor working or unplugged?? Just used my fon for the clock. Breakfast area very clean and orderly and good. Parking lot had potholes but they were there fixing them today. Staff VERY friendly!!! "
A verified traveler stayed at Quality Inn Old Saybrook - Westbrook
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