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Top Southold hotels

Vine & Sand

Vine & Sand

3 out of 5
47100 New York 25 Southold NY
$415 nightly
The price is $474 total per night from May 18 to May 19
$474 total
May 18 - May 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
Fully refundableReserve now, pay when you stay
$169 nightly
The price is $193 total per night from May 21 to May 22
$193 total
May 21 - May 22
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 ...
Amazing. Loved everything about this place and will be back. The rooms were surprisingly spacious and the decor was perfect. I wish the pool was opened but I guess only for true summer. A great value and we will be back.

Reviewed on May 16, 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
$243 nightly
The price is $274 total per night from May 31 to Jun 1
$274 total
May 31 - Jun 1
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.
Very helpful staff. Room was very roomy (no pun intented) and appeared to be recently upgraded. Chit provided for continental breakfast at a local coffee shop that was very good. Definitely recommend.

Reviewed on May 5, 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 May 25 to May 26
$360 total
May 25 - May 26
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 ...
Nice room and view

Reviewed on May 15, 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
$175 nightly
The price is $200 total per night from May 19 to May 20
$200 total
May 19 - May 20
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 ...
The breakfast was delicious, the rooms were nice, and the bar was perfect. In all of my travels I think the staff at this hotel might be the nicest, most accommodating people I’ve ever met. They truly made our stay wonderful. Olga and the other front desk staff were amazing.

Reviewed on May 8, 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 ...
Bedding was suboptimal and toilets clogged. Additionally, very noisy due to 2 weddings in the resort that night… so not very relaxing.

Reviewed on May 17, 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
$292 nightly
The price is $334 total per night from May 19 to May 20
$334 total
May 19 - May 20
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 ...
This is a beautiful place in a great town. Greenport has much to recommend it. Excellent restaurants, interesting shopping, and congenial places to hang around, have a drink, a pastry or coffee. The seafood, from shellfish to the top of the maritime food chain is fresh and abundant, and generally ...

Reviewed on May 17, 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
$370 nightly
The price is $422 total per night from May 19 to May 20
$422 total
May 19 - May 20
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 ...
They charged us for parking in front of our room. Unbelievable. We stayed there in April, off season, the motel was empty.

Reviewed on May 11, 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
$92 nightly
The price is $105 total per night from May 18 to May 19
$105 total
May 18 - May 19
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 have been coming here for years and it is the best it’s ever been! Staff is friendly and accommodating. The rooms have been renovated and clean.

Reviewed on May 17, 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 $105. 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 4,438 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

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

5 out of 5
Posted 5 hours ago
Travelocity Verified Review
"We have been coming here for years and it is the best it’s ever been! Staff is friendly and accommodating. The rooms have been renovated and clean."
A verified traveler stayed at Pier Blue Inn Old Saybrook - Essex
Pier Blue Inn Old Saybrook - Essex

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