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Compare 4,339 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Terrace/patio
Capri
3.5 star property
6.4 out of 10, (218)
"The rooms are grrat with all details"
The price is $359
$435 total
includes taxes & fees
May 21 - May 22
Capri
Front of property
The Wainscott Inn
3.0 star property
8.6 out of 10, Excellent, (92)
"Looks like the were in the process of updating? Lots of construction people and debris but we also went during off season so it made sense. Have to drive everywhere but still convenient!! "
The price is $294
$371 total
includes taxes & fees
Jun 16 - Jun 17
The Wainscott Inn
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 $269
$338 total
includes taxes & fees
May 20 - May 21
The Pridwin Hotel
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Aerial view
East Hampton Art House Bed & Breakfast
4.0 star property
9.8 out of 10, Exceptional, (54)
"Beautiful property and Michael and Rosealind are some the nicest hosts we have ever encountered. "
The price is $762
$869 total
includes taxes & fees
May 20 - May 21
East Hampton Art House Bed & Breakfast
Cottage, 1 Bedroom (with porch - Pet Friendly + Fee) | Private kitchen | Dishwasher, coffee/tea maker
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 $127
$144 total
includes taxes & fees
May 30 - May 31
Hampton's Vacation Inn
Deluxe Studio | Living area | TV
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 $315
$381 total
includes taxes & fees
May 21 - May 22
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, (373)
"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 $159
$188 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)
"We stayed in the cottage and it was very well appointed decor wise. Cute common areas where breakfast is. The room could have used another light in the LR and it needed a desk and a better closet. No place to put the luggage and tiny closet. Could be furnished a bit better to accomodate. Overall very nice stay. Tx!"
The price is $325
$408 total
includes taxes & fees
May 27 - May 28
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 $500
$599 total
includes taxes & fees
May 22 - May 23
Canoe Place Inn and Cottages
Property amenity
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 $595
$713 total
includes taxes & fees
May 20 - May 21
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 $450
$514 total
includes taxes & fees
May 20 - May 21
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 Maidstone
Property grounds
Hampton Maid Motel
2.5 star property
8.8 out of 10, Excellent, (523)
"The property is well kept and beautiful. I will definitely come back. "
The price is $203
$231 total
includes taxes & fees
May 20 - May 21
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 $199
$237 total
includes taxes & fees
May 27 - May 28
Southampton Long Island Hotel
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 $249
$284 total
includes taxes & fees
May 20 - May 21
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 $429
$538 total
includes taxes & fees
May 27 - May 28
EHP Resort & Marina
View from property
House on Chase Creek
2.5 star property
9.4 out of 10, Exceptional, (64)
"Amazing location. Lovely lake. Serene and Tranquil experience. "
The price is $276
$315 total
includes taxes & fees
May 20 - May 21
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 $455
$519 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
Outdoor spa tub
The Drake Inn
2.0 star property
9.0 out of 10, Wonderful, (77)
"The hotel was very clean and the location was very good. It was close to restaurants and beach."
The Drake Inn
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Southold Travel Info

Number of reviews
3,063
Accommodation
4,339 hotels
Highest price
$762
Lowest price
$93

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 Hilton Garden Inn Riverhead and Residence Inn by Marriott New York Long Island East End. See all available top hotels, or vacation rentals in Southold.

What's the top vacation rental in Southold?

Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool: This vacation home rental outside of Southold offers an outdoor pool, a fireplace, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. It offers a balcony, 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 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.

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