Find hotels in Southold, NY from $93

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May 16 - May 17
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May 17 - May 18
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May 17 - May 19
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May 24 - May 26

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Compare 4,328 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

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 $299
$375 total
includes taxes & fees
May 19 - May 20
The Pridwin Hotel
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
Exterior
Chic & Serene in The Hamptons. 1 block to waterside dining and the best sunsets
10.0 out of 10, Exceptional, (1)
"Friends and I stayed the weekend at this rental and loved it! We cooked, watched a movie, played board games, and enjoyed the fall weather. It is in a quiet neighborhood that is an easy drive to town, beaches, and nature preserves. Lisa is a very responsive and gracious host! Would definitely recommend!"
Chic & Serene in The Hamptons. 1 block to waterside dining and the best sunsets
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Garden
The Farmhouse Bed and Breakfast
3.5 star property
10.0 out of 10, Exceptional, (5)
"The Farmhouse was a perfect stay for a relaxing weekend in beautiful surroundings. The Farmhouse is charming and impeccably kept. The hosts are friendly and amazing cooks. Added plus : a destination charger for our Tesla! Definitely recommend!"
The Farmhouse Bed and Breakfast
Exterior
East Hampton Classic Close to Bay Beaches w/Private Backyard, Heated Pool & Deck
10.0 out of 10, Exceptional, (69)
"We loved staying here! The pool and back yard were perfect for relaxing days in the sun, and the kitchen and grill made group dinners easy. The location is quiet, but close enough to town for convenience. We would definitely stay here again!"
East Hampton Classic Close to Bay Beaches w/Private Backyard, Heated Pool & Deck
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
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 $595
$713 total
includes taxes & fees
May 19 - May 20
The Roundtree, Amagansett
Property grounds
The Hedges Inn
3.5 star property
9.6 out of 10, Exceptional, (66)
"Beautiful location and lovely accommodation."
The Hedges Inn
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 $250
$285 total
includes taxes & fees
May 19 - May 20
Colonial Shores Resort
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 entrance
Southampton Village Motel
2.5 star property
9.2 out of 10, Wonderful, (42)
"My room was unacceptable, there was mold and the shower was flooding the bathroom all the time, the wifi did not work very well and the owner/manager was not helpful. I had to call every time we needed more towels and she was not welcoming or friendly at all. When we told her about the shower she did not show any remorse"
The price is $399
$455 total
includes taxes & fees
May 19 - May 20
Southampton Village Motel
Smart TV
Location and views! Located directly on Shinnecock Bay!
9.2 out of 10, Wonderful, (11)
"Since I stay for 2 days only it was fine. Check the shades , toilet paper and more towels. "
Location and views! Located directly on Shinnecock Bay!
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 $127
$144 total
includes taxes & fees
May 28 - May 29
Hampton's Vacation Inn
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 $203
$231 total
includes taxes & fees
May 20 - May 21
Hampton Maid Motel
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
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 $321
$388 total
includes taxes & fees
May 20 - May 21
East Hampton House 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 $293
$367 total
includes taxes & fees
May 30 - May 31
Journey East Hampton
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
$565 total
includes taxes & fees
May 19 - May 20
Mill House Inn
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 $146
$174 total
includes taxes & fees
May 20 - May 21
Bayview Resort
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See all available properties in Southold
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.

More cheap stays in Southold

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

100 Essex Rd, Old Saybrook, CT
The price is $93 per night from May 27 to May 28
$93
$107 total
includes taxes & fees
May 27 - May 28
7.4/10 Good! (957 reviews)

Stay near popular Southold attractions

Image for Sparkling Pointe

Sparkling Pointe

You can enjoy a tasting or tour at Sparkling Pointe during your travels to Southold. Discover the sunsets and wineries in this family-friendly area.

See properties
Sparkling Pointe

Southold Travel Info

Number of reviews
3,376
Accommodation
4,328 hotels
Highest price
$806
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 are some accommodations with pools in Southold?

Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower is a top B&B with a communal pool, an in-room fireplace, and a spa tub. A couple of other options with an onsite pool include Vine + Sand--Southold, NY'S Newest B&B--Room 1--King Bed and Ensuite Bathroom With Soaking Tub and Vine + Sand--Southold, NY'S Newest B&B Room--Room 3--Queen Bed and Ensuite Bathroom With Rain Shower. 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.

Recent reviews of Southold hotels
Expedia verified reviews

The Atlantic Hotel

The Atlantic Hotel

5/5 Excellent
Non Hampton prices.
"Great prices, huge room, convenient and super friendly staff. Have stayed the past 3 weeks for business, good location"
A verified traveler stayed at The Atlantic Hotel
Posted 1 day ago
The Atlantic Hotel