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Top Southold hotels

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
$135 nightly
The price is $154 total per night from Oct 31 to Nov 1
$154 total
Oct 31 - Nov 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 ...
"Gorgeous room! Felt like we were home"

Reviewed on Oct 20, 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
$210 nightly
The price is $237 total per night from Nov 4 to Nov 5
$237 total
Nov 4 - Nov 5
Total with taxes and fees
A communal living room, a picnic area, and express check-out are available at this hotel. Wedding services are provided for your convenience.
"We had a 2 bedroom. It was tight in the rooms. It met our needs for a couple of nights. I thought it was expensive based on its location behind a boat marina."

Reviewed on Oct 20, 2026

Opens in a new windowThe Shoals Suites and Slips
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
$216 nightly
The price is $248 total per night from Nov 22 to Nov 23
$248 total
Nov 22 - Nov 23
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 ...
"Great"

Reviewed on Oct 21, 2026

Opens in a new windowWater's Edge Resort & Spa
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
$82 nightly
The price is $94 total per night from Nov 15 to Nov 16
$94 total
Nov 15 - Nov 16
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 ...
"I stayed twice and borh rooms were decorated uniquely. The staff and owners were very nice. Good people"

Reviewed on Oct 21, 2026

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
$131 nightly
The price is $150 total per night from Nov 22 to Nov 23
$150 total
Nov 22 - Nov 23
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 ...
"We were 4 girls and the room was two bedrooms and another bed also so it accommodated all of us. 😊"

Reviewed on Oct 19, 2026

Opens in a new windowThe Atlantic Hotel
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
$167 nightly
The price is $191 total per night from Nov 22 to Nov 23
$191 total
Nov 22 - Nov 23
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 ...
Opens in a new windowSound View Greenport
Zey Hotel

Zey Hotel

3.5 out of 5
439 Main Street Greenport NY
$164 nightly
The price is $187 total per night from Nov 5 to Nov 6
$187 total
Nov 5 - Nov 6
Total with taxes and fees
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
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

2.5 out of 5
100 Essex Rd Old Saybrook CT
Fully refundable
$97 nightly
The price is $111 total per night from Nov 11 to Nov 12
$111 total
Nov 11 - Nov 12
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
Greenview Inn Riverhead

Greenview Inn Riverhead

2 out of 5
1433 W Main St Riverhead NY
Fully refundableReserve now, pay when you stay
$102 nightly
The price is $117 total per night from Nov 10 to Nov 11
$117 total
Nov 10 - Nov 11
Total with taxes and fees
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.
Opens in a new windowGreenview Inn Riverhead
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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 $94. 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 4,294 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 2 hours ago
Travelocity Verified Review
"Great"
A verified traveler stayed at Water's Edge Resort & Spa
Water's Edge Resort & Spa

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