Book Hotels in Southold, NY

Start date: Check-in selected.
To Date
End date: Check-out

Cabins, apartments, houseboats! We offer comfortable & private vacation rentals

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Filter by

Guest rating
Guest rating
Star rating
Payment type
Payment type
Property type
Property type
Neighborhood
Neighborhood
Traveler experience
Traveler experience
Popular locations
Popular locations
Meal plans available
Meal plans available
Amenities
Amenities
Accessibility
Accessibility

Top Southold hotels

The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 out of 5
61600 Main Rd Southold NY
$174 nightly
The price is $199 total per night from Jan 7 to Jan 8
$199 total
Jan 7 - Jan 8, 2026
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

Opens in a new windowThe Shoals Suites and Slips
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5
2 Bridge St Old Saybrook CT
Fully refundableReserve now, pay when you stay
$311 nightly
The price is $358 total per night from Dec 23 to Dec 24
$358 total
Dec 23 - Dec 24
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 stay with Saybrook Point Resort & Marina was amazing. Clean room, amazing staff and amenities! I plan to return again!

Reviewed on Dec 8, 2025

Opens in a new windowSaybrook Point Resort & Marina
The Bentley Hotel Southampton

The Bentley Hotel Southampton

2 out of 5
161 Hills Station Rd Southampton NY
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $133 total per night from Dec 15 to Dec 16
$133 total
Dec 15 - Dec 16
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 ...
Had a wonderful stay at The Bentley Hotel Southampton. The room was spacious, stylish, and spotless. I especially loved the record player — such a unique and thoughtful touch that made the stay feel personal and relaxing. The overall vibe of the room and the layout were perfect. Staff were friendly ...

Reviewed on Dec 7, 2025

Opens in a new windowThe Bentley Hotel Southampton
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
$244 nightly
The price is $281 total per night from Dec 10 to Dec 11
$281 total
Dec 10 - Dec 11
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 ...
Yes! Ease of registration! The staff helped us with dinning suggestions, hotel programs and amenities!

Reviewed on Dec 7, 2025

Opens in a new windowWater's Edge Resort & Spa
The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
209 Front St Greenport NY
$153 nightly
The price is $175 total per night from Dec 24 to Dec 25
$175 total
Dec 24 - Dec 25
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 ...
Yes

Reviewed on Dec 8, 2025

Opens in a new windowThe Harbor Front Inn
The Sagaponack

The Sagaponack

3 out of 5
3720 Montauk Hwy Wainscott NY
$185 nightly
The price is $212 total per night from Dec 22 to Dec 23
$212 total
Dec 22 - Dec 23
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

Opens in a new windowThe Sagaponack
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
$197 nightly
The price is $225 total per night from Dec 24 to Dec 25
$225 total
Dec 24 - Dec 25
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

Opens in a new windowSound View Greenport
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
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

Opens in a new windowPier Blue Inn Old Saybrook - Essex
The Atlantic Hotel

The Atlantic Hotel

2.5 out of 5
1655 County Road 39 Southampton NY
$138 nightly
The price is $158 total per night from Jan 6 to Jan 7
$158 total
Jan 6 - Jan 7, 2026
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

Opens in a new windowThe Atlantic Hotel
Don't see what you're looking for?
See all available properties in Southold
View all properties
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

What are the top kid-friendly hotels in Southold?
Family getaways are where the best memories are made, but it's no secret that traveling with youngsters can be tricky. These kid-friendly Southold hotels come with perks designed to keep adventurers of all ages relaxed and happy: The Stucco House will help make your next trip the most memorable one yet. It features an assortment of conveniences geared toward families, such as a king bed and a fireplace. Otherwise, spend your nights in Southold at Idyllic waterfront home with dock, kayaks, bikes, firepit, & fireplace - dogs OK. Make the most of cycling, a king bed and more here.
Where can I find cheap hotels in Southold?
At Travelocity you'll find really nice hotels in Southold at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Southold rather than in Southold. We may find you even better rates, too.
How do I find the best Southold hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Southold then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Southold?
The cheapest hotel in Southold is $91. This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Southold?
There are 4,301 hotels in Southold on Travelocity.
What are the best hotels in Southold?
Southold has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Southold for you!
When is the best time to visit Southold?
If you want the joy of a fun-filled trip in peak season, visit Southold during May, June and July. If you'd prefer the peace of off-season, book a stay during quieter months, such as January, October and December.
When is the cheapest time to stay in Southold?
Based on historic data is usually the cheapest month to visit Southold. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Southold?
There are multiple hotels in Southold that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Southold. We have plenty of kid-friendly hotels in Southold to choose from on Travelocity!
Why book a hotel in Southold through Travelocity?
Because we have the top hotels in Southold! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Southold on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Southold hotel reviews by fellow wanderers

The Harbor Front Inn

The Harbor Front Inn

5 out of 5
Posted 1 day ago
Travelocity Verified Review
"Yes"
A verified traveler stayed at The Harbor Front Inn
The Harbor Front Inn

Explore More Ways to Travel with Travelocity