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May 2 - May 3
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May 3 - May 4
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May 3 - May 5
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May 10 - May 12

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Top Trending Hotels Near The Heights, Shelter Island Heights

Seasonal outdoor pool, pool umbrellas, pool loungers
The Pridwin Hotel
3.0 star property
10.0 out of 10, Exceptional, (19)
"Very elegant "
The price is £299
includes taxes & fees
13 May - 14 May
The Pridwin Hotel
Seasonal outdoor pool
Hotel Moraine
2.0 star property
10.0 out of 10, Exceptional, (12)
"Beautiful hotel, great location. Wish someone was at the front desk all night though."
The price is £300
includes taxes & fees
5 May - 6 May
Hotel Moraine
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 £459
includes taxes & fees
22 May - 23 May
Canoe Place Inn and Cottages
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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
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
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 £379
includes taxes & fees
6 May - 7 May
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 £569
includes taxes & fees
5 May - 6 May
The Roundtree, Amagansett
Private beach, sun-loungers, beach umbrellas, beach towels
Silver Sands
2.5 star property
9.8 out of 10, Exceptional, (38)
"Everything was wonderful-staff, cleanliness, great weather and good food at Nookies 😃"
The price is £314
includes taxes & fees
5 May - 6 May
Silver Sands
Dock
Stirling House Bed & Breakfast
3.0 star property
9.8 out of 10, Exceptional, (21)
"This was a great place to stay with old word charm. If you are looking for a quiet getaway with a beautiful view of the ocean this is it. The breakfast that we had were much better that what you could get in town. My wife and I can't wait to go back."
Stirling House Bed & Breakfast
Flat-screen TV, fireplace, pay films
Harbor Knoll Bed & Breakfast
3.0 star property
9.8 out of 10, Exceptional, (6)
"Beautiful, private oceanfront property right next to all the restaurants in town. "
The price is £301
includes taxes & fees
6 May - 7 May
Harbor Knoll Bed & Breakfast
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 £200
includes taxes & fees
5 May - 6 May
Colonial Shores Resort
View from property
House on Chase Creek
2.5 star property
9.4 out of 10, Exceptional, (63)
"The owner is very friendly and helpful. He even upgraded the room without additional fee. The rooms are so clean and organized with nice thick towels and amenities. Free coffee and tea were available with a water server, microwave, and a little sink to wash dishes. The area is so quiet and peaceful although some good restaurants and ferry port are in walking distance. Highly recommended. "
The price is £160
includes taxes & fees
6 May - 7 May
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 £363
includes taxes & fees
5 May - 6 May
Southampton Village Motel
Exterior
Arbor View House B&B
3.5 star property
9.2 out of 10, Wonderful, (13)
"This house was old but beautiful and decorated nicely inside. "
Arbor View House B&B
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 £115
includes taxes & fees
28 May - 29 May
Hampton's Vacation Inn
Beach nearby
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (179)
"Always a very nice time staying at this property. The sunset on the beach was amazing. Convenient to all area restaurants, wineries, breweries and Matchbook Distilling. "
The price is £259
includes taxes & fees
5 May - 6 May
Cliffside Resort Condominiums
Reception
American Beech Hotel
3.5 star property
9.0 out of 10, Wonderful, (152)
"A beautiful and very relaxing place to stay. Really appreciated the little touches like a breakfast basket delivered to your doorstep in the morning! Very friendly and helpful staff too. Perfect place for a Long Island getaway! "
The price is £242
includes taxes & fees
16 May - 17 May
American Beech Hotel
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)
"Great stay and clean beautiful rooms"
The price is £275
includes taxes & fees
16 May - 17 May
East Hampton House Resort
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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.

The Heights Travel Info

Location
Shelter Island Heights, United States of America
Number of hotels
3,980
Known landmarks
Crescent Beach, Sylvester Manor and Sunset Beach
Hotels with nearby beaches
Sound View Greenport, American Beech Hotel and Cliffside Resort Condominiums

Frequently asked questions

What is The Heights like?

Guests are sure to enjoy their time checking out all that Shelter Island Heights's The Heights neighbourhood has to offer. Make sure that you visit Sunset Beach and Shelter Island Country Club as part of your The Heights travel plans.

Where is the best place to stay in The Heights?

Based on Expedia customer reviews, House on Chase Creek is the highest ranked property in The Heights. This guest house offers free parking and free WiFi. Another top choice in the area is The Chequit.

How many hotels can I expect to find in the The Heights area?

If you're searching for places to stay in Shelter Island Heights, choose from one of Expedia's 13 hotels and other accommodation options in The Heights.

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

Yes! You'll find that most hotel bookings are fully refundable as long as you cancel before the accommodation's cancellation deadline, which is usually within 24-48 hours of the scheduled arrival. If you booked a non-refundable reservation, you may still be able to cancel and get a refund within a 24-hour period of your booking. Enter your dates, click on "Search", then you can filter by "fully refundable" to review the top deals on offer in The Heights.

What are the top things to see and do in The Heights?

A few attractions you might want to check out while you're in The Heights are Sunset Beach and Shelter Island Country Club. While you're out sightseeing, Sylvester Manor and Crescent Beach are a couple of additional sights to visit in Shelter Island Heights.

The Heights Hotel Reviews

Madison Beach Hotel

Madison Beach Hotel

5/5 Excellent
"The staff was extremely courteous and professional. Location ideal."
A verified traveller stayed at Madison Beach Hotel
Posted 1 day ago
Madison Beach Hotel