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Aug 16 - Aug 17
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Aug 17 - Aug 18
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Aug 21 - Aug 23

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 center
The price is CA $403 per night
CA $403
CA $496 total
Sep 1 - Sep 2
includes taxes & fees
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
Restaurant
Vine & Sand

Vine & Sand

3 out of 5
47100 New York 25 Southold NY
2.12 km from city center
Get rates
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.
Pool
Breakfast included
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Free cancellation
24.68 km from city center
The price is CA $133 per night
CA $133
CA $153 total
Sep 10 - Sep 11
includes taxes & fees
Stay at this hotel in Old Saybrook. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chalker Beach and Crystal Lake Town Park are located nearby.
Pet-friendly
Parking included
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
4.24 km from city center
The price is CA $363 per night
CA $363
CA $533 total
Sep 9 - Sep 10
includes taxes & fees
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 Hashamomuck Pond and Railroad Museum of Long Island are located nearby.
On private beach
Pool
The Atlantic Hotel

The Atlantic Hotel

2.5 out of 5
1655 County Road 39 Southampton NY
18.95 km from city center
The price is CA $273 per night
CA $273
CA $347 total
Sep 8 - Sep 9
includes taxes & fees
Stay at this hotel in Southampton. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Cooper's Beach and Sebonack Golf Course are located nearby.
Pool
Pet-friendly
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
Free cancellation
Reserve now, pay when you stay
24.1 km from city center
The price is CA $323 per night
CA $323
CA $396 total
Sep 14 - Sep 15
includes taxes & fees
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.
On private beach
Pool
North Fork Resort

North Fork Resort

3 out of 5
690 Queen St Greenport NY
5.81 km from city center
The price is CA $436 per night
CA $436
CA $498 total
Sep 16 - Sep 17
includes taxes & fees
Stay at this cottage in Greenport. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Railroad Museum of Long Island and Greenport Farmers' Market are located nearby.
Pool
Pet-friendly
Hampton's Vacation Inn

Hampton's Vacation Inn

2.5 out of 5
177 West Montauk Highway Hampton Bays NY
23.27 km from city center
The price is CA $281 per night
CA $281
CA $321 total
Aug 31 - Sep 1
includes taxes & fees
Stay at this guesthouse in Hampton Bays. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Regal UA Hampton Bays and Good Ground Park are located nearby.
Pool
Pet-friendly
The Pridwin Hotel

The Pridwin Hotel

4 out of 5
81 Shore Road Shelter Island Heights NY
4.29 km from city center
The price is CA $741 per night
CA $741
CA $932 total
Sep 13 - Sep 14
includes taxes & fees
Book a stay at this beach hotel in Shelter Island Heights. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Crescent Beach and Sunset Beach are located nearby.
On private beach
Pool
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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.

Top hotels in Southold for Extended Stay

Canoe Place Waterfront Residences

Canoe Place Waterfront Residences

239 E Montauk Hwy Hampton Bays NY
10/10 Exceptional! (2 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
4,362 hotels
Lowest Price
CA $153
Highest Price
CA $932
Popular hotels
The Shoals Suites and Slips, Vine & Sand, Pier Blue Inn Old Saybrook - Essex, Sound View Greenport, The Atlantic Hotel, Water's Edge Resort & Spa, North Fork Resort, Hampton's Vacation Inn, The Pridwin 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 $153 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 4,362 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 11 hours ago
Travelocity Verified Review
"The vibe of PBG didn’t quite match up with my original expectations for a coastal beachside inn, but we had a great time. This was largely due to a room upgrade upon arrival and the kindness of the inn keeper. I’d request a room at the back of the property, which has a gorgeous view out onto the marshes and faces the West so the sunrise doesn’t rain in through your window in the morning. The bed was very comfortable, the rooms were quiet despite being on a main road, and the AC worked great. Oh, and hot tip. The Tea Kettle restaurant across the road has a fantastic breakfast."
A verified traveller stayed at Pier Blue Inn Old Saybrook - Essex
Pier Blue Inn Old Saybrook - Essex