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Top Southold hotels

Vine & Sand

Vine & Sand

3 out of 5
47100 New York 25 Southold NY
$351 nightly
The price is $401 total per night from Apr 29 to Apr 30
$401 total
Apr 29 - Apr 30
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
Fully refundableReserve now, pay when you stay
$164 nightly
The price is $187 total per night from Apr 30 to May 1
$187 total
Apr 30 - May 1
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 ...
The property was just as described and we couldn't have been more pleasantly surprised when we arrived after the long trek thru what seemed like nothingness between NYC and Southampton. At 1st glance we were a bit skeptical, but upon entry found the property ti be a hidden gem. We even extended our ...

Reviewed on Apr 26, 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
$213 nightly
The price is $240 total per night from Apr 28 to Apr 29
$240 total
Apr 28 - Apr 29
Total with taxes and fees
This hotel features a bar/lounge, a coffee shop, and a communal living room. A business center, a picnic area, and express check-out are also on offer.
My girlfriend and I stayed in April and it was amazing stay. Rooms are outstanding, one of the best rooms we ever stayed, and location was stunning. Beautiful marina, great waterfront views from the property. It was so quiet and relaxing. We went to Greenport for dinners. 10$ Breakfast cards were ...

Reviewed on Apr 25, 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
$225 nightly
The price is $257 total per night from Apr 29 to Apr 30
$257 total
Apr 29 - Apr 30
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 hotel. Very clean, very friendly staff, great water pressure. Breakfast was continental... Fruit, cereal, yogurt, muffins. Fresh coffee. Overall nice experience.

Reviewed on Apr 26, 2026

Opens in a new windowSag Harbor Inn
Hyatt Place Long Island East End

Hyatt Place Long Island East End

3 out of 5
451 East Main Street Riverhead NY
Fully refundableReserve now, pay when you stay
$147 nightly
The price is $168 total per night from May 6 to May 7
$168 total
May 6 - May 7
Total with taxes and fees
A marina and an outdoor pool are featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public ...
Breakfast is better than most chain hotels. Clean and friendly staff near lots of good food options.

Reviewed on Apr 22, 2026

Opens in a new windowHyatt Place Long Island East End
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
$264 nightly
The price is $304 total per night from May 20 to May 21
$304 total
May 20 - May 21
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 ...
Was very nice used hotels.com saved alot for both rooms. Enkoyed the pool and spa hot tub was great. Pricy but worth it the view was beautiful

Reviewed on Apr 25, 2026

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
$224 nightly
The price is $256 total per night from Apr 28 to Apr 29
$256 total
Apr 28 - Apr 29
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 ...
Great

Reviewed on Apr 23, 2026

Opens in a new windowThe Harbor Front Inn
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
$252 nightly
The price is $288 total per night from May 3 to May 4
$288 total
May 3 - May 4
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 ...
This is a lovely motel located right on the Sound and all rooms face the water. The room was clean and relatively spacious, though most of the space was devoted to the kitchen and living areas. The bathroom was a bit small, as was the sleeping area. My family, including an elderly relative, traveled ...

Reviewed on Apr 21, 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
$91 nightly
The price is $104 total per night from May 3 to May 4
$104 total
May 3 - May 4
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 ...
The hotel is in pretty rough shape. The sink rusted, the tub and mirror dirty. The garbage cans still had garbage from the previous guests. The only good part was the location

Reviewed on Apr 24, 2026

Opens in a new windowPier Blue Inn Old Saybrook - Essex
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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 $104. 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 4,425 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

Sag Harbor Inn

Sag Harbor Inn

5 out of 5
Posted 10 hours ago
Travelocity Verified Review
"Lovely hotel. Very clean, very friendly staff, great water pressure. Breakfast was continental... Fruit, cereal, yogurt, muffins. Fresh coffee. Overall nice experience. "
A verified traveler stayed at Sag Harbor Inn
Sag Harbor Inn

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