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Apr 15 - Apr 16
Tomorrow
Apr 16 - Apr 17
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Apr 18 - Apr 20
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Apr 25 - Apr 27

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Compare 4,269 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

The Shoals Suites and Slips
Garden Suite King

The Shoals Suites and Slips

3.5 star property
9.4 out of 10, Exceptional, (156)
"Great stay! Would come back again. "
The price is CA $261
CA $333 total
includes taxes & fees
Apr 16 - Apr 17
The Shoals Suites and Slips
Ocean Vista Resort
View from property

Ocean Vista Resort

2.5 star property
9.0 out of 10, Wonderful, (173)
"Came for business, wonderful location by the beach. Quiet and comfortable. The only real downside (which is kind of a big deal) there was no coffee/tea. There is a coffee maker, you need to bring your own ground beans. That was odd, even airbnb"s supply some coffee. Would have been nice to know om advance"
Ocean Vista Resort
Windward Shores Ocean Resort
Ocean View 2BD Corner King and Queen | Private kitchen

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (282)
"Condo was great, family of 5 , clean, no hassle"
The price is CA $198
CA $256 total
includes taxes & fees
Apr 16 - Apr 17
Windward Shores Ocean Resort
The Roundtree, Amagansett
Frette Italian sheets, premium bedding, down comforters

The Roundtree, Amagansett

4.5 star property
9.8 out of 10, Exceptional, (85)
"My wife and I stayed a couple nights in October. We felt very pampered. Felix served us up late night snacks with homemade cookies and ice cream! Beautiful and charming hotel with attentive staff."
The price is CA $963
CA $1,156 total
includes taxes & fees
Apr 23 - Apr 24
The Roundtree, Amagansett
The Reform Club
Deluxe Suite

The Reform Club

2.0 star property
10.0 out of 10, Exceptional, (1)
"We went to the area for a last minute concert. We loved all the staff and the property was exquisite. We would like to recommend that if you are sensitive to noise you should stay in the upstairs suites. High quality and we will be back if ever in this area in the future."
The price is CA $1,344
CA $1,720 total
includes taxes & fees
Apr 23 - Apr 24
The Reform Club
Journey East Hampton
Exterior

Journey East Hampton

4.0 star property
9.2 out of 10, Wonderful, (129)
"Clean and up to date "
The price is CA $406
CA $510 total
includes taxes & fees
Apr 16 - Apr 17
Journey East Hampton
East Hampton House Resort
Studio

East Hampton House Resort

3.0 star property
9.0 out of 10, Wonderful, (248)
"Perfect location and super clean"
The price is CA $227
CA $290 total
includes taxes & fees
Apr 29 - Apr 30
East Hampton House Resort
Mill House Inn
Front of property - evening/night

Mill House Inn

5.0 star property
9.0 out of 10, Wonderful, (68)
"What a lovely space and wonderful thoughtful staff! Absolutely loved everything about it, and the breakfast was beyond excellence! Hats off to the chef you can tell she cooked with ❤️ love. Highly Recommend you experience it for yourself. "
The price is CA $451
CA $567 total
includes taxes & fees
Apr 16 - Apr 17
Mill House Inn
East Hampton Art House Bed & Breakfast
Aerial view

East Hampton Art House Bed & Breakfast

4.0 star property
9.6 out of 10, Exceptional, (61)
"What a beautiful, quiet, peaceful place to stay, even in the dead of winter. The home itself is modern, welcoming, bright, everything you could dream of. The hosts are very active and successful artists who all but gave us a private master class in how their work is imagined and created. I don’t know when we’ve had a more delightful weekend. The walks to the beach were lovely, too. "
The price is CA $578
CA $660 total
includes taxes & fees
May 12 - May 13
East Hampton Art House Bed & Breakfast
The Huntting Inn
Exterior

The Huntting Inn

3.5 star property
8.6 out of 10, Excellent, (87)
"One of the very few options in East Hampton that offered a one night stay, most have a 2-night minimum. An old, charming inn that was very welcoming and clean. Our king bed room was spacious enough and decorated nicely. The bathroom was very clean and modernized. We did have to walk up a flight of stairs with our luggage which wasn’t difficult for us but may be for some."
The price is CA $565
CA $660 total
includes taxes & fees
May 4 - May 5
The Huntting Inn
The 1770 House Restaurant & Inn
Reception

The 1770 House Restaurant & Inn

4.0 star property
9.8 out of 10, Exceptional, (149)
"Loved the property. Well kept and very quaint. Room was comfortable and immaculate. We ate at the restaurant for dinner. Food and service were amazing. Can’t say enough good things about this place. Highly recommend. Does not disappoint. "
The price is CA $343
CA $469 total
includes taxes & fees
Apr 22 - Apr 23
The 1770 House Restaurant & Inn
The Maidstone
Front of property - evening/night

The Maidstone

4.0 star property
7.8 out of 10, Good, (121)
"Excellent stay!"
The price is CA $361
CA $413 total
includes taxes & fees
Apr 27 - Apr 28
The Maidstone
EHP Resort & Marina
Cottage

EHP Resort & Marina

3.5 star property
7.8 out of 10, Good, (8)
"Beautiful property and the cottages were clean, gorgeous, and comfortable. It was just hard to get in touch with anyone for service related issues. The restaurant on site, Si Si was amazing and the staff there went above and beyond!"
The price is CA $479
CA $602 total
includes taxes & fees
Apr 16 - Apr 17
EHP Resort & Marina
The Sagaponack
Exterior

The Sagaponack

3.0 star property
8.8 out of 10, Excellent, (146)
"It’s okay for a night or two not a first or second choice however. The cosmetic upgrade for this property is okay in comparison to the cost of the stay. The doors only have a button lock on some cottages and seems like the original handle, it was loose and the key was sticking. Though I was accommodated with a different cottage that had a padlock as well, there was a visible mold and moisture issue causing the laminate floors to bubble. Some groundskeeping opportunities with pathways and the...
The price is CA $255
CA $362 total
includes taxes & fees
Apr 20 - Apr 21
The Sagaponack
A Room At The Beach
Outdoor pool

A Room At The Beach

3.0 star property
9.0 out of 10, Wonderful, (83)
"Beautiful property and amazing staff, I will definitely be back soon!"
The price is CA $611
CA $698 total
includes taxes & fees
Apr 16 - Apr 17
A Room At The Beach
Topping Rose House
Outdoor pool

Topping Rose House

4.5 star property
9.2 out of 10, Wonderful, (131)
"Had an excellent stay at Topping Rose House! Can’t wait to be back soon!"
The price is CA $526
CA $606 total
includes taxes & fees
Apr 16 - Apr 17
Topping Rose House
The Niantic Inn
Premium bedding, individually decorated, individually furnished, desk

The Niantic Inn

2.0 star property
9.2 out of 10, Wonderful, (89)
"Loved this hotel! Friendly staff and extremely clean. I plan on coming back. The only place I will stay."
The price is CA $165
CA $190 total
includes taxes & fees
Apr 16 - Apr 17
The Niantic Inn
Bridgehampton Inn
Property grounds

Bridgehampton Inn

3.5 star property
9.4 out of 10, Exceptional, (213)
"Lovely inn, with very accommodating staff. "
The price is CA $415
CA $474 total
includes taxes & fees
Apr 22 - Apr 23
Bridgehampton Inn
Baron's Cove
Front of property - evening/night

Baron's Cove

4.0 star property
9.0 out of 10, Wonderful, (226)
"Excellent stay while visiting our son!"
Baron's Cove
Sag Harbor Inn
Outdoor pool

Sag Harbor Inn

3.5 star property
9.4 out of 10, Exceptional, (508)
"Great cozy stay. Very nice staff, amazing location."
The price is CA $298
CA $341 total
includes taxes & fees
Apr 16 - Apr 17
Sag Harbor Inn
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.
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Learn more about Southold

Come to Southold and enjoy its wineries, island views, and beaches.

See all hotels in Southold

Frequently asked questions

Where is the best place to stay in Southold?

The Shoals Suites and Slips is one of the top choices for your stay based on our traveler data. This hotel offers a restaurant and private balconies. Other good choices for your trip to the area are Water's Edge Resort & Spa and Pier Blue Inn Old Saybrook - Essex. See all available top hotels, or vacation rentals in Southold.

What's the top vacation rental in Southold?

Stunning Hampton Holiday Family Fantasy for your Team : This vacation home rental outside Southold is located in a rural location and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation. See all vacation rentals in Southold.

If I need to cancel my hotel reservation in Southold, will I receive a refund?

Yes, the majority of room reservations are refundable provided that you cancel prior to the hotel's cancellation deadline, which is often 24 or 48 hours before the scheduled arrival. If your reservation is non-refundable, you might still have the option to cancel and be given a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Southold.

Where can I learn more about changing or cancelling my trip to Southold?

To access more information about rescheduling or cancelling your trip to Southold, head over to our customer service page.

What's the best hotel for couples in Southold?

The Shoals Suites and Slips is a favorite hotel for couples, and features wedding services and free breakfast. See all romantic hotels in Southold.

What's the best pet-friendly accommodation in Southold?

White Blossom House Inn is a top hotel for people traveling with their pets, and offers free use of bicycles and in-room kitchens for its human guests. Cozy Long Island Escape is another option for you and your pet. See more pet-friendly hotel accommodations in Southold.

Where is the best hotel to stay near Sparkling Pointe?

White Blossom House Inn is one of the top choices for your stay based on our traveler data, and this hotel offers free parking and private patios. It's located just a short 0.9 mi (1.4 km) from Sparkling Pointe.

What about the best place to stay close to Mattebella Vineyards?

One of the top choices for your stay is White Blossom House Inn, located a short 0.7 mi (1.1 km) from Mattebella Vineyards, and this hotel offers free parking and private patios.

What's the best accommodation to stay near the beach in Southold?

Shorecrest Bed and Breakfast is a top beach B&B with free breakfast and free WiFi, and it's located close to Crescent Beach. See more stays near the beach in Southold.

What's the best high-end hotel in Southold?

Vine & Sand is a luxury B&B with a private beach and a seasonal outdoor pool, and it's a popular choice for Expedia travelers looking for an elegant place to stay. Find more luxury hotels in Southold.

What are some accommodations with pools in Southold?

Water's Edge Resort & Spa: Features a seasonal outdoor pool, an indoor pool, and a private beach. Hyatt Place Long Island East End and Baron's Cove are a couple of other choices that feature an onsite pool. View all hotels with pools in Southold.

What is the best spa hotel in Southold?

Shorecrest Bed and Breakfast is a top spa hotel with 5 rooms, free WiFi, and a fireplace in the lobby. Enjoy a massage at the on-site spa. See all spa hotels in Southold.

What's the best place to stay near John F. Kennedy International Airport (JFK)?

Holiday Inn Express Kennedy Airport is a popular hotel, featuring free breakfast and free WiFi. It's located a short 1.5 mi (2.5 km) from John F. Kennedy Intl. Airport. Other options near the airport are Fairfield Inn by Marriott JFK Airport and Radisson Hotel JFK Airport.

What's it like to stay in Southold?

Visitors can enjoy all that Southold has to offer including the wineries, beaches, and gardens. Tourists can also enjoy the city's football games and monuments. In Southold, there are 159 hotels and other accommodations to choose from. Find out more about Southold.

What should I see while I'm in Southold?

Favorite places to visit include Sparkling Pointe, Croteaux Vineyards, and Osprey's Dominion. A couple of additional sights to add to your agenda are Sannino's Bella Vita Vineyard and The Old Field Vineyards. Check out what more to see and do in Expedia's Southold guide.

How should I get around Southold?

To see more of the larger area, hop aboard a train at Southold Station. If you want to venture out around the area, you may want a rental car in Southold for your journey.

What's the weather like in Southold?

The hottest months are usually August and July with an average temp of 70°F, while the coldest months are January and February with an average of 38°F. Average annual precipitation for Southold is 57 inches.