Book Cheap Hotels in Southold

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Check hotel availability in Southold

Tonight
Check prices in Southold for tonight, May 27 - May 28
May 27 - May 28
Tomorrow night
Check prices in Southold for tomorrow night, May 28 - May 29
May 28 - May 29
This weekend
Check prices in Southold for this weekend, May 29 - May 31
May 29 - May 31
Next weekend
Check prices in Southold for next weekend, Jun 5 - Jun 7
Jun 5 - Jun 7

Most frequently booked Southold hotels

The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 out of 5
61600 Main Rd Southold NY
2.28 km from city centre
The price is CA $301 per night
CA $301
per night
May 31 - Jun 1
Stay at this hotel in Southold. Enjoy free WiFi, free bicycles on site, and a business center. Our guests praise the helpful staff in our reviews. Popular attractions The Old Field Vineyards and Crescent Beach are located nearby.
Free WiFi
Air conditioning
Vine & Sand

Vine & Sand

3 out of 5
47100 New York 25 Southold NY
2.12 km from city centre
The price is CA $545 per night
CA $545
per night
May 28 - May 29
Book a stay at this business-friendly B&B in Southold. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Mattebella Vineyards and Croteaux Vineyards are located nearby.
The Bentley Hotel Southampton

The Bentley Hotel Southampton

2 out of 5
161 Hills Station Rd Southampton NY
19.23 km from city centre
The price is CA $283 per night
CA $283
per night
May 28 - May 29
Book a stay at this business-friendly hotel in Southampton. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Cooper's Beach and Sebonack Golf Course are located nearby.
Pool
Pet-friendly
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
4.24 km from city centre
The price is CA $374 per night
CA $374
per night
May 28 - May 29
Book a stay at this beach hotel in Greenport. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Railroad Museum of Long Island and The Old Field Vineyards are located nearby.
On private beach
Pool
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
24.1 km from city centre
The price is CA $293 per night
CA $293
per night
May 31 - Jun 1
Book a stay at this beach resort in Westbrook. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Tanger Outlets and Westbrook Town Beach are located nearby.
Sag Harbor Inn

Sag Harbor Inn

3.5 out of 5
45 West Water Street Sag Harbor NY
12.64 km from city centre
The price is CA $435 per night
CA $435
per night
May 31 - Jun 1
Book a stay at this business-friendly hotel in Sag Harbor. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions The Hamptons Beaches and Sag Harbor Whaling and Historical Museum are located nearby.
Pool
Breakfast included
The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
209 Front St Greenport NY
6.75 km from city centre
The price is CA $372 per night
CA $372
per night
May 28 - May 29
Book a stay at this business-friendly hotel in Greenport. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Greenport Carousel and Camera Obscura are located nearby.
Pool
Breakfast included
Hyatt Place Long Island East End

Hyatt Place Long Island East End

3 out of 5
451 East Main Street Riverhead NY
25.22 km from city centre
The price is CA $351 per night
CA $351
per night
Jun 2 - Jun 3
Book a stay at this business-friendly hotel in Riverhead. Enjoy free WiFi, free parking, and a marina. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Splish Splash Water Park and Suffolk Theater are located nearby.
Zey Hotel

Zey Hotel

3.5 out of 5
439 Main Street Greenport NY
7.08 km from city centre
The price is CA $224 per night
CA $224
per night
Jun 2 - Jun 3
Book a stay at this boutique hotel in Greenport. Enjoy free parking, free bicycles on site, and daily housekeeping. Popular attractions Greenport Harbor Brewing Company and Greenport Farmers' Market are located nearby.
Pet-friendly
Parking included
Don't see what you're looking for?
See all available properties in Southold
View all properties
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.

Top hotels in Southold for Extended Stay

The modern farmhouse view

The modern farmhouse view

East Quogue NY
10/10 Exceptional! (9 reviews)
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.

Southold hotels essential information

Accommodation
4,466 hotels
Lowest Price
CA $255
Highest Price
CA $623
Popular hotels
The Shoals Suites and Slips, Vine & Sand, The Bentley Hotel Southampton, Sound View Greenport, Water's Edge Resort & Spa, Sag Harbor Inn, The Harbor Front Inn, Hyatt Place Long Island East End, Zey Hotel

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 CA $255 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 4,466 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 less than an hour ago
Travelocity Verified Review
"nice harbour views , lovely high street and restaurants nearby"
A verified traveller stayed at Sag Harbor Inn
Sag Harbor Inn