Book Hotels in Southold, NY

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Top Southold hotels

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
The price is $251 total per night from Oct 7 to Oct 8
$251 total
per night
Oct 7 - Oct 8
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 grounds and the interior of the property were beautifully maintained and tastefully appointed. The staff is exceptionally friendly. The bathroom in my room was dated and needed remodeling. Wall dispensers of shampoo, conditioner and body wash were not installed in shower as is generally offered ..."

Reviewed on Sep 21, 2026

Opens in a new windowWater's Edge Resort & Spa
Greenview Inn Riverhead

Greenview Inn Riverhead

2 out of 5
1433 W Main St Riverhead NY
Fully refundableReserve now, pay when you stay
The price is $132 total per night from Oct 21 to Oct 22
$132 total
per night
Oct 21 - Oct 22
Free self parking is available and the motel's front desk is staffed around-the-clock. WiFi in public areas is free. A garden is also provided.
"No lovks in doors, bathroom flooded, the person who checked me in was barefoot. I plan to dispute this charge!!!"

Reviewed on Sep 20, 2026

Opens in a new windowGreenview Inn Riverhead
The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 out of 5
61600 Main Rd Southold NY
The price is $286 total per night from Oct 1 to Oct 2
$286 total
per night
Oct 1 - Oct 2
A restaurant and a bar/lounge are featured at this hotel. A business center, a communal living room, and a picnic area are also on offer.
Opens in a new windowThe Shoals Suites and Slips
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
The price is $93 total per night from Oct 8 to Oct 9
$93 total
per night
Oct 8 - Oct 9
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 ...
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
The price is $161 total per night from Oct 4 to Oct 5
$161 total
per night
Oct 4 - Oct 5
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 ...
Opens in a new windowThe Atlantic Hotel
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
The price is $302 total per night from Oct 21 to Oct 22
$302 total
per night
Oct 21 - Oct 22
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 ...
Opens in a new windowSound View Greenport
Zey Hotel

Zey Hotel

3.5 out of 5
439 Main Street Greenport NY
The price is $193 total per night from Oct 5 to Oct 6
$193 total
per night
Oct 5 - Oct 6
A bar/lounge and a coffee shop are featured at this hotel, along with free self parking. WiFi in public areas is free. A terrace, a garden, and a picnic area ...
Opens in a new windowZey Hotel
The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
209 Front St Greenport NY
The price is $281 total per night from Oct 19 to Oct 20
$281 total
per night
Oct 19 - Oct 20
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 ...
Opens in a new windowThe Harbor Front Inn
Budget Host East End

Budget Host East End

2 out of 5
30 Lake Avenue Riverhead NY
Fully refundableReserve now, pay when you stay
The price is $102 total per night from Sep 29 to Sep 30
$102 total
per night
Sep 29 - Sep 30
A seasonal outdoor pool, free self parking, and barbecue grills are featured at this motel. WiFi in public areas is free. A safe deposit box is provided and ...
Opens in a new windowBudget Host East End
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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 $93. 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 4,302 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

Water's Edge Resort & Spa

Water's Edge Resort & Spa

5 out of 5
Posted 7 hours ago
Travelocity Verified Review
"The grounds and the interior of the property were beautifully maintained and tastefully appointed. The staff is exceptionally friendly. The bathroom in my room was dated and needed remodeling. Wall dispensers of shampoo, conditioner and body wash were not installed in shower as is generally offered in most 4 star hotels. While there is a coffee machine in guest rooms, there is no complimentary coffee offered in the lobby."
A verified traveler stayed at Water's Edge Resort & Spa
Water's Edge Resort & Spa

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