Find hotels in Southold, NY from CA $122

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Top 10 Southold hotels and places to stay

Terrace/patio
Capri
3.5 star property
6.4 out of 10, (218)
"The rooms are grrat with all details"
The price is CA $545
CA $660 total
includes taxes & fees
May 19 - May 20
Capri
Seasonal outdoor pool, pool umbrellas, sun loungers
The Pridwin Hotel
3.0 star property
10.0 out of 10, Exceptional, (20)
"Everything was exquisite! "
The price is CA $408
CA $512 total
includes taxes & fees
May 16 - May 17
The Pridwin Hotel
Aerial view
East Hampton Art House Bed & Breakfast
4.0 star property
9.8 out of 10, Exceptional, (53)
"Beautiful property and Michael and Rosealind are some the nicest hosts we have ever encountered. "
The price is CA $1,040
CA $1,187 total
includes taxes & fees
May 16 - May 17
East Hampton Art House Bed & Breakfast
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Children's activities
Hampton's Vacation Inn
2.5 star property
9.0 out of 10, Wonderful, (234)
"The bathroom was very clean with nice plush towels. The room was also very clean with a comfortable bed. I would definitely recommend this Inn to my friends and relatives. Great location as well!"
The price is CA $173
CA $197 total
includes taxes & fees
May 28 - May 29
Hampton's Vacation Inn
Outdoor pool
Topping Rose House
4.5 star property
9.4 out of 10, Exceptional, (105)
"Noise from other guests."
The price is CA $949
CA $1,088 total
includes taxes & fees
May 22 - May 23
Topping Rose House
Deluxe Studio | Living area
East Hampton House Resort
3.0 star property
8.8 out of 10, Excellent, (227)
"Very convenient with own entrance and back deck and parking right in front!! Can walk to dining and breakfast options or make in your own kitchen nook!! "
The price is CA $438
CA $529 total
includes taxes & fees
May 22 - May 23
East Hampton House Resort
Seasonal outdoor pool, open 8:00 AM to 8:30 PM, free cabanas
Bayview Resort
2.5 star property
8.6 out of 10, Excellent, (372)
"The view of the bay is incredible ( I was on 2nd floor) but the structure itself needs some t l c, fresh paint, more tables in room, etc. "
The price is CA $200
CA $237 total
includes taxes & fees
May 20 - May 21
Bayview Resort
Exterior
Journey East Hampton
4.0 star property
8.8 out of 10, Excellent, (88)
"Loved the room, bed was comfortable, shower was lovely. Cindy gave great suggestions on where to go."
The price is CA $399
CA $501 total
includes taxes & fees
May 29 - May 30
Journey East Hampton
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas
Canoe Place Inn and Cottages
4.0 star property
10.0 out of 10, Exceptional, (26)
"Absolutely the nicest hotel in the area. "
The price is CA $683
CA $818 total
includes taxes & fees
May 22 - May 23
Canoe Place Inn and Cottages
Beach nearby, white sand, sun loungers, beach umbrellas
The Roundtree, Amagansett
4.5 star property
9.8 out of 10, Exceptional, (75)
"The best hotel in the Hamptons! Luxury hospitality without pretension. Quiet, simple and the only one worth the price tag. You will pay the same if not more at any other local hotel and receive the worst service. It would be so easy for Roundtree to just rely on the high summer months to make money and rob you because they can, but they don't. The whole team works with an integrity uncommon to the area. Easy walk to everything in town and while they don't have a restaurant or bar they make up...
The price is CA $812
CA $973 total
includes taxes & fees
May 19 - May 20
The Roundtree, Amagansett
Front of property - evening/night
Mill House Inn
5.0 star property
8.8 out of 10, Excellent, (50)
"Excellent facility and excellent service. Highly recommend. "
The price is CA $614
CA $771 total
includes taxes & fees
May 19 - May 20
Mill House Inn
Front of property - evening/night
The Maidstone
4.0 star property
7.8 out of 10, Good, (112)
"Staff was very friendly and engaging. Handled all of our needs wonderfully."
The price is CA $1,085
CA $1,239 total
includes taxes & fees
May 23 - May 24
The Maidstone
Property grounds
Hampton Maid Motel
2.5 star property
9.0 out of 10, Wonderful, (522)
"The property is well kept and beautiful. I will definitely come back. "
The price is CA $276
CA $316 total
includes taxes & fees
May 16 - May 17
Hampton Maid Motel
Desk, free WiFi, bed sheets
Southampton Long Island Hotel
2.5 star property
8.4 out of 10, Very good, (165)
"Awesome stay -- room was very clean and bed was really comfortable. They also upgraded us to a deluxe room at no charge! Would stay again. "
The price is CA $272
CA $324 total
includes taxes & fees
May 17 - May 18
Southampton Long Island Hotel
Porch
Harpoon House
3.0 star property
8.2 out of 10, Very good, (103)
"very friendly host "
The price is CA $496
CA $567 total
includes taxes & fees
May 28 - May 29
Harpoon House
Aerial view
Colonial Shores Resort
2.5 star property
9.4 out of 10, Exceptional, (81)
"This is our second 8 day stay. Here for work (Hanging Wallpaper) we really enjoyed our time here. Around the corner from everything. "
The price is CA $341
CA $390 total
includes taxes & fees
May 19 - May 20
Colonial Shores Resort
2 restaurants, breakfast, lunch, dinner served; Mediterranean cuisine
EHP Resort & Marina
3.5 star property
7.8 out of 10, Good, (7)
"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 $586
CA $735 total
includes taxes & fees
May 28 - May 29
EHP Resort & Marina
View from property
House on Chase Creek
2.5 star property
9.4 out of 10, Exceptional, (63)
"543y"
The price is CA $377
CA $430 total
includes taxes & fees
May 16 - May 17
House on Chase Creek
Property grounds
Bridgehampton Inn
3.5 star property
9.4 out of 10, Exceptional, (205)
"I will never NOT stay there when I’m in the area. The restaurant should have a Michelin star and the cocktails were inventive and delicious. The rooms had fireplaces- it was perfect on a storm night. The coffee is was excellent and the beds soft. If I could give it 10 stars, I would."
The price is CA $621
CA $709 total
includes taxes & fees
May 20 - May 21
Bridgehampton Inn
1 bedroom, WiFi, bed sheets
Sag Harbor Suite by the Beach
9.0 out of 10, Wonderful, (8)
"We were in town to celebrate thanksgiving. Nice cozy 1 bedroom apartment. 5 minute drive to town."
Sag Harbor Suite by the Beach
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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

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 free breakfast and a restaurant. Other good choices for your trip to the area are Quality Inn Old Saybrook - Westbrook and Hilton Garden Inn Riverhead. See all available top hotels, or vacation rentals in Southold.

What's the top vacation rental in Southold?

Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!: This vacation home rental outside of Southold is located next to a golf course and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games. 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 good 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 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 163 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 Sannino's Bella Vita Vineyard. A couple of additional sights to add to your agenda are The Old Field Vineyards and Mattebella 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.