Book Hotels in Southold, NY
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Top Southold hotels

The Shoals Suites and Slips
61600 Main Rd Southold NY
$174 nightly
The price is $199 total per night from Dec 29 to Dec 30
$199 total
Dec 29 - Dec 30
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 luggage storage are also on offer.
My o
Reviewed on Nov 24, 2025

Saybrook Point Resort & Marina
2 Bridge St Old Saybrook CT
Fully refundableReserve now, pay when you stay
$312 nightly
The price is $359 total per night from Dec 15 to Dec 16
$359 total
Dec 15 - Dec 16
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 ...
Excellent food, in addition to friendly and helpful staff.
Reviewed on Dec 1, 2025

The Bentley Hotel Southampton
161 Hills Station Rd Southampton NY
Fully refundableReserve now, pay when you stay
$118 nightly
The price is $135 total per night from Dec 11 to Dec 12
$135 total
Dec 11 - Dec 12
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 ...
Clean and quiet.
Reviewed on Nov 30, 2025

Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
$210 nightly
The price is $242 total per night from Dec 16 to Dec 17
$242 total
Dec 16 - Dec 17
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 ...
Staff
Reviewed on Nov 30, 2025

The Harbor Front Inn
209 Front St Greenport NY
$174 nightly
The price is $199 total per night from Dec 29 to Dec 30
$199 total
Dec 29 - Dec 30
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 ...
Always love staying there when in Greenport. Clean. Central. Quality continental breakfast.
Reviewed on Nov 24, 2025

The Sagaponack
3720 Montauk Hwy Wainscott NY
$184 nightly
The price is $211 total per night from Dec 15 to Dec 16
$211 total
Dec 15 - Dec 16
Total with taxes and fees
A seasonal outdoor pool is featured at this bed & breakfast, along with free self parking. WiFi in public areas is free. A communal living room and luggage storage ...
Clean & amenities, staff friendly Thank you
Reviewed on Dec 2, 2025

Sound View Greenport
58775 County Rd 48 Greenport NY
$237 nightly
The price is $271 total per night from Jan 8 to Jan 9
$271 total
Jan 8 - Jan 9, 2026
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 ...
Great room with amazing views! Staff was fantastic and the food was great too
Reviewed on Nov 28, 2025

Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundableReserve now, pay when you stay
$79 nightly
The price is $91 total per night from Dec 21 to Dec 22
$91 total
Dec 21 - Dec 22
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 ...
A welcoming place with some nice touches.
Reviewed on Nov 30, 2025

The Atlantic Hotel
1655 County Road 39 Southampton NY
$138 nightly
The price is $158 total per night from Dec 23 to Dec 24
$158 total
Dec 23 - Dec 24
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 ...
Great hotel for a quick stay - very friendly staff
Reviewed on Nov 24, 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

The Sagaponack
5 out of 5
Posted 6 days ago
Travelocity Verified Review
"Clean & amenities, staff friendly
Thank you "
A verified traveler stayed at The Sagaponack
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