Book Hotels in Southold, NY
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Top Southold hotels

Vine & Sand
47100 New York 25 Southold NY
The price is $431 total per night from Apr 14 to Apr 15
$431 total
per night
Apr 14 - Apr 15
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
The price is $160 total per night from Apr 1 to Apr 2
$160 total
per night
Apr 1 - Apr 2
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 ...
Loved the place, clean and helpfull staff.
Reviewed on Mar 30, 2026

The Shoals Suites and Slips
61600 Main Rd Southold NY
The price is $197 total per night from Apr 13 to Apr 14
$197 total
per night
Apr 13 - Apr 14
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.
Simply delightful!
Reviewed on Mar 30, 2026

Hyatt Place Long Island East End
451 East Main Street Riverhead NY
Fully refundableReserve now, pay when you stay
The price is $162 total per night from Apr 29 to Apr 30
$162 total
per night
Apr 29 - Apr 30
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 ...
Did not use
Reviewed on Mar 27, 2026

Residence Inn by Marriott New York Long Island East End
2012 Old Country Road Riverhead NY
Fully refundableReserve now, pay when you stay
The price is $169 total per night from Apr 26 to Apr 27
$169 total
per night
Apr 26 - Apr 27
2 hot tubs, an indoor pool, and a 24-hour gym are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center ...
Loved it
Reviewed on Mar 28, 2026

Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
The price is $285 total per night from Apr 9 to Apr 10
$285 total
per night
Apr 9 - Apr 10
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 ...
Enjoyable stay.
Reviewed on Mar 28, 2026

Hilton Garden Inn Riverhead
2038 Old Country Rd Riverhead NY
Fully refundableReserve now, pay when you stay
The price is $154 total per night from Apr 12 to Apr 13
$154 total
per night
Apr 12 - Apr 13
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the indoor pool and perks like free self parking and free WiFi. Enjoy the gym and ...
This hotel is such a wonderful place to stay… the manager JC is very nice, all the staff including Victoria… we love going there.. and the food in the hotel restaurant is delicious. my husband and I will be back.
Reviewed on Mar 30, 2026

Sound View Greenport
58775 County Rd 48 Greenport NY
The price is $230 total per night from Apr 19 to Apr 20
$230 total
per night
Apr 19 - Apr 20
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 ...
it was ok
Reviewed on Mar 30, 2026

The Harbor Front Inn
209 Front St Greenport NY
The price is $209 total per night from Apr 14 to Apr 15
$209 total
per night
Apr 14 - Apr 15
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 ...
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
1 out of 5
Posted 10 hours ago
Travelocity Verified Review
"My room was no where near clean. Not only was there multiple urine stains on the toilet seat, there was also a fecal stain that was also not cleaned IN the toilet. How do you not clean the TOILET? "
A verified traveler stayed at Pier Blue Inn Old Saybrook - Essex
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