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Top Southold hotels

Vine & Sand

Vine & Sand

3 out of 5
47100 New York 25 Southold NY
$538 nightly
The price is $614 total per night from Jun 18 to Jun 19
$614 total
Jun 18 - Jun 19
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

Opens in a new windowVine & Sand
The Bentley Hotel Southampton

The Bentley Hotel Southampton

2 out of 5
161 Hills Station Rd Southampton NY
$166 nightly
The price is $190 total per night from Jun 7 to Jun 8
$190 total
Jun 7 - Jun 8
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 ...
"Really nice place to stay - recommend it every much"

Reviewed on May 29, 2026

Opens in a new windowThe Bentley Hotel Southampton
The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 out of 5
61600 Main Rd Southold NY
$267 nightly
The price is $302 total per night from Jun 4 to Jun 5
$302 total
Jun 4 - Jun 5
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.
"Everything was better than advertised. We will definitely stay again."

Reviewed on May 31, 2026

Opens in a new windowThe Shoals Suites and Slips
Sag Harbor Inn

Sag Harbor Inn

3.5 out of 5
45 West Water Street Sag Harbor NY
$315 nightly
The price is $360 total per night from Jun 2 to Jun 3
$360 total
Jun 2 - Jun 3
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 ...
"Great location, room was spacious with great outlook and breakfast was perfect!"

Reviewed on May 30, 2026

Opens in a new windowSag Harbor Inn
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
$266 nightly
The price is $306 total per night from Jun 11 to Jun 12
$306 total
Jun 11 - Jun 12
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 ...
"The location and the amenities provided by the hotel was first classed"

Reviewed on May 27, 2026

Opens in a new windowWater's Edge Resort & Spa
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
$450 nightly
The price is $514 total per night from Jun 2 to Jun 3
$514 total
Jun 2 - Jun 3
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 ...
"Love being on the water"

Reviewed on May 31, 2026

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 refundable
$98 nightly
The price is $112 total per night from Jun 7 to Jun 8
$112 total
Jun 7 - Jun 8
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 ...
"We used the place as a crash pad - easy to get to from the marina and close to "the main strip" . We did not have a car and it was a holiday weekend."

Reviewed on May 28, 2026

Opens in a new windowPier Blue Inn Old Saybrook - Essex
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

2.5 out of 5
100 Essex Rd Old Saybrook CT
Fully refundable
$118 nightly
The price is $136 total per night from Jun 21 to Jun 22
$136 total
Jun 21 - Jun 22
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will ...
"Everyone was friendly, the rooms were clean and breakfast was great!"

Reviewed on May 30, 2026

Opens in a new windowQuality Inn Old Saybrook - Westbrook
The Atlantic Hotel

The Atlantic Hotel

2.5 out of 5
1655 County Road 39 Southampton NY
$221 nightly
The price is $252 total per night from Jun 2 to Jun 3
$252 total
Jun 2 - Jun 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 ...
"Overall, I had a pleasant stay at this hotel. The room was comfortable, clean upon arrival, and the staff were friendly and helpful when contacted. The only issue I encountered was that I wasn't aware daily housekeeping was not included during my stay. As a result, I had to call the front desk to ..."

Reviewed on May 30, 2026

Opens in a new windowThe Atlantic Hotel
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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 $112. 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 4,466 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 Shoals Suites and Slips

The Shoals Suites and Slips

5 out of 5
Posted 13 hours ago
Travelocity Verified Review
"Everything was better than advertised. We will definitely stay again."
A verified traveler stayed at The Shoals Suites and Slips
The Shoals Suites and Slips

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