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Hotels in The Heights, Shelter Island Heights from CA $173

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The Heights hotels and places to stay

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 $409
CA $513 total
includes taxes & fees
May 16 - May 17
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 CA $391
CA $513 total
includes taxes & fees
May 15 - May 16
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 CA $684
CA $819 total
includes taxes & fees
May 22 - May 23
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
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 $569
CA $649 total
includes taxes & fees
May 15 - May 16
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 CA $813
CA $975 total
includes taxes & fees
May 15 - May 16
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 CA $472
CA $538 total
includes taxes & fees
May 15 - May 16
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 CA $451
CA $515 total
includes taxes & fees
May 21 - May 22
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 CA $342
CA $390 total
includes taxes & fees
May 15 - May 16
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 CA $377
CA $431 total
includes taxes & fees
May 15 - May 16
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 CA $545
CA $622 total
includes taxes & fees
May 15 - May 16
Southampton Village Motel
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
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 CA $336
CA $443 total
includes taxes & fees
May 15 - May 16
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 CA $277
CA $316 total
includes taxes & fees
May 16 - May 17
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 CA $313
CA $398 total
includes taxes & fees
May 27 - May 28
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 CA $430
CA $521 total
includes taxes & fees
May 16 - May 17
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 CA $400
CA $502 total
includes taxes & fees
May 27 - May 28
Journey East Hampton
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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 neighborhood has to offer. Be sure to check out 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 guesthouse offers free parking and free WiFi. Another top choice in the area is The Chequit.

How many hotels will I 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 accommodations in The Heights.

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

Yes, most hotel bookings are fully refundable if cancelled prior to the hotel's cancellation deadline, which is usually within 24-48 hours of your scheduled arrival. If you have a reservation that's non-refundable, you may still be able to cancel and get a refund within 24 hours of your booking. Plug in your dates, click on "Search", then use the "fully refundable" filter to get the best options available in The Heights.

Where can I learn more about changing or cancelling my trip to The Heights?

To find more details about picking new dates or cancelling your trip to The Heights, click here.

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.