Book Hotels in Southold, NY

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Top Southold hotels

Vine & Sand

Vine & Sand

3 out of 5
47100 New York 25 Southold NY
$348 nightly
The price is $398 total per night from Apr 29 to Apr 30
$398 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
$170 nightly
The price is $194 total per night from Apr 29 to Apr 30
$194 total
Apr 29 - Apr 30
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 29 to Apr 30
$240 total
Apr 29 - Apr 30
Total with taxes and fees
This hotel features a bar/lounge, a coffee shop, and a communal living room. A business center, a picnic area, and express check-out are also on offer.
My girlfriend and I stayed in April and it was amazing stay. Rooms are outstanding, one of the best rooms we ever stayed, and location was stunning. Beautiful marina, great waterfront views from the property. It was so quiet and relaxing. We went to Greenport for dinners. 10$ 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 ...
So clean! Loved the location.

Reviewed on Apr 27, 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
$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 ...
It is a lovely hotel.

Reviewed on Apr 28, 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 29 to Apr 30
$256 total
Apr 29 - Apr 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 ...
Spacious, well appointed rooms. Great location. The complimentary breakfast was cozy (nothing fancy but gets the job done). We stayed for three nights with a small dog in tow. The only surprise was that parking was not free ($29 per night) but there was plenty of free street parking available ...

Reviewed on Apr 27, 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 ...
Clean hotel , comfortable room, beautiful views, quiet place, EZ access to the beach. Coming back for summer

Reviewed on Apr 27, 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 7 to May 8
$104 total
May 7 - May 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 ...
Good location

Reviewed on Apr 27, 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 May 19 to May 20
$136 total
May 19 - May 20
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 ...
Opens in a new windowQuality Inn Old Saybrook - Westbrook
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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 4,434 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

Madison Beach Hotel

Madison Beach Hotel

5 out of 5
Posted 18 hours ago
Travelocity Verified Review
"Excellent hotel, high quality in every way, beautiful setting, very quiet relaxing and peaceful Sunday night stay off-season."
A verified traveler stayed at Madison Beach Hotel
Madison Beach Hotel

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