Photo by Erisa Dilo

The Heights Hotels, Shelter Island Heights

Most accommodation are fully refundable. Because flexibility matters.

Save an average of 15% on thousands of hotels with Expedia Rewards

Search over 2.9 million properties and 550 airlines worldwide

Find properties with these dates

Tonight
May 14 - May 15
Tomorrow
May 15 - May 16
This weekend
May 17 - May 19
Next weekend
May 24 - May 26

Filter by

Popular filters
Popular filters
Total price
Guest rating
Guest rating
Property class
Payment type
Payment type
Property type
Property type
Area
Area
Popular locations
Popular locations
Meal plans available
Meal plans available
Amenities
Amenities
Accessibility
Accessibility
Traveller experience
Traveller experience

4007 Cheap Hotels in The Heights - Specials, Reviews, & Last Minute Deals

Seasonal outdoor pool, pool umbrellas, pool loungers
The Pridwin Hotel
3.0 star property
10.0 out of 10, Exceptional, (20)
"Everything was exquisite! "
The price is NZ$567
per night
15 May - 16 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 NZ$542
per night
15 May - 16 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 NZ$929
per night
22 May - 23 May
Canoe Place Inn and Cottages
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
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
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 NZ$1,128
per night
15 May - 16 May
The Roundtree, Amagansett
Private beach, sun-loungers, beach umbrellas, beach towels
Silver Sands
2.5 star property
9.8 out of 10, Exceptional, (41)
"We absolutely loved our stay at Silver Sands. The vibe was amazing! The retro styling and overall ambience sets the tone for a relaxing and unforgettable get away. The staff was professional and incredible friendly. The attention to detail was phenomenal. I highly recommended having breakfast at their dinner as well. Trust me you can't go wrong if you stay at Silver Sands."
The price is NZ$654
per night
16 May - 17 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
Living area
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 NZ$626
per night
15 May - 16 May
Harbor Knoll Bed & Breakfast
Seasonal outdoor pool
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 NZ$474
per night
15 May - 16 May
Colonial Shores Resort
View from property
House on Chase Creek
2.5 star property
9.4 out of 10, Exceptional, (63)
"543y"
The price is NZ$523
per night
15 May - 16 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 NZ$756
per night
15 May - 16 May
Southampton Village Motel
Front of property
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 NZ$240
per night
28 May - 29 May
Hampton's Vacation Inn
Beach nearby
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (181)
"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 NZ$466
per night
15 May - 16 May
Cliffside Resort Condominiums
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 NZ$384
per night
15 May - 16 May
Hampton Maid Motel
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 NZ$434
per night
27 May - 28 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
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 NZ$608
per night
22 May - 23 May
East Hampton House 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 NZ$555
per night
28 May - 29 May
Journey East Hampton
Don't see what you're looking for?
See all available properties in The Heights
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

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.