Photo by Erisa Dilo

Hotels in The Heights, Shelter Island Heights from CA $148

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Check prices for these dates

Tonight
Feb 22 - Feb 23
Tomorrow
Feb 23 - Feb 24
Next weekend
Feb 28 - Mar 2
In two weeks
Mar 7 - Mar 9

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The Heights hotels and places to stay

House on Chase Creek
View from property

House on Chase Creek

2.5 star property
9.4 out of 10, Exceptional, (67)
"Everything you need for a stay on the island"
The price is CA $148
CA $168 total
includes taxes & fees
Mar 25 - Mar 26
House on Chase Creek
The Chequit
Outdoor dining

The Chequit

3.0 star property
8.8 out of 10, Excellent, (28)
"Excellent "
The price is CA $450
CA $513 total
includes taxes & fees
Feb 23 - Feb 24
The Chequit
Sea Crest Resort
Studio Unit Upper Oceanfront 'San Remo' | Terrace/patio

Sea Crest Resort

2.5 star property
9.2 out of 10, Wonderful, (446)
"The only problem I had is with a shade on a door , bad design not hotel’s problem. And that I wanted to rebook for another time and no matter what dates I put in they weren’t available "
The price is CA $315
CA $390 total
includes taxes & fees
Feb 23 - Feb 24
Sea Crest Resort
The Hermitage
Seasonal outdoor pool

The Hermitage

3.5 star property
9.2 out of 10, Wonderful, (153)
"Access to the dunes and the beach "
The price is CA $228
CA $291 total
includes taxes & fees
Mar 25 - Mar 26
The Hermitage
Windward Shores Ocean Resort
View from property

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (273)
"Beautiful location, clean property, and nice staff. Just hard to turn in to the parking lot but not much that the hotel can do for that. The private beach is stunning. "
The price is CA $187
CA $244 total
includes taxes & fees
Mar 23 - Mar 24
Windward Shores Ocean Resort
The Roundtree, Amagansett
Beach nearby, white sand, sun loungers, beach umbrellas

The Roundtree, Amagansett

4.5 star property
9.8 out of 10, Exceptional, (85)
"My wife and I stayed a couple nights in October. We felt very pampered. Felix served us up late night snacks with homemade cookies and ice cream! Beautiful and charming hotel with attentive staff."
The price is CA $985
CA $1,181 total
includes taxes & fees
Mar 2 - Mar 3
The Roundtree, Amagansett
Journey East Hampton
Exterior

Journey East Hampton

4.0 star property
9.0 out of 10, Wonderful, (124)
"Enjoyed our stay here. Room was spacious. Really friendly staff. "
The price is CA $277
CA $362 total
includes taxes & fees
Feb 24 - Feb 25
Journey East Hampton
East Hampton House Resort
Deluxe Studio | Living area

East Hampton House Resort

3.0 star property
9.0 out of 10, Wonderful, (245)
"Perfect location and super clean"
The price is CA $231
CA $294 total
includes taxes & fees
Mar 18 - Mar 19
East Hampton House Resort
Mill House Inn
Front of property - evening/night

Mill House Inn

5.0 star property
9.0 out of 10, Wonderful, (67)
"What a lovely space and wonderful thoughtful staff! Absolutely loved everything about it, and the breakfast was beyond excellence! Hats off to the chef you can tell she cooked with ❤️ love. Highly Recommend you experience it for yourself. "
The price is CA $354
CA $445 total
includes taxes & fees
Feb 27 - Feb 28
Mill House Inn
East Hampton Art House Bed & Breakfast
Aerial view

East Hampton Art House Bed & Breakfast

4.0 star property
9.6 out of 10, Exceptional, (61)
"What a beautiful, quiet, peaceful place to stay, even in the dead of winter. The home itself is modern, welcoming, bright, everything you could dream of. The hosts are very active and successful artists who all but gave us a private master class in how their work is imagined and created. I don’t know when we’ve had a more delightful weekend. The walks to the beach were lovely, too. "
The price is CA $599
CA $683 total
includes taxes & fees
Feb 26 - Feb 27
East Hampton Art House Bed & Breakfast
The Huntting Inn
Exterior

The Huntting Inn

3.5 star property
8.6 out of 10, Excellent, (87)
"One of the very few options in East Hampton that offered a one night stay, most have a 2-night minimum. An old, charming inn that was very welcoming and clean. Our king bed room was spacious enough and decorated nicely. The bathroom was very clean and modernized. We did have to walk up a flight of stairs with our luggage which wasn’t difficult for us but may be for some."
The price is CA $653
CA $759 total
includes taxes & fees
Mar 24 - Mar 25
The Huntting Inn
The 1770 House Restaurant & Inn
Reception

The 1770 House Restaurant & Inn

4.0 star property
9.8 out of 10, Exceptional, (147)
"Property was adorable and the staff very pleasant and helpful!! "
The price is CA $357
CA $487 total
includes taxes & fees
Mar 2 - Mar 3
The 1770 House Restaurant & Inn
The Maidstone
Front of property - evening/night

The Maidstone

4.0 star property
7.8 out of 10, Good, (120)
"Overall good experience, FYI, restaurant/bar is closed during off season. :("
The price is CA $440
CA $502 total
includes taxes & fees
Mar 24 - Mar 25
The Maidstone
The Sagaponack
Exterior

The Sagaponack

3.0 star property
8.8 out of 10, Excellent, (136)
"TV too high. Cannot reset if goes off proper setting. Need to stand on chair. "
The price is CA $197
CA $275 total
includes taxes & fees
Feb 23 - Feb 24
The Sagaponack
Topping Rose House
Outdoor pool

Topping Rose House

4.5 star property
9.2 out of 10, Wonderful, (125)
"Topping Rose House is beautiful, and the staff is excellent. I am looking forward to returning on my next visit"
The price is CA $562
CA $646 total
includes taxes & fees
Feb 26 - Feb 27
Topping Rose House
The Niantic Inn
Beach nearby

The Niantic Inn

2.0 star property
9.2 out of 10, Wonderful, (86)
"We loved our stay!"
The price is CA $200
CA $231 total
includes taxes & fees
Mar 25 - Mar 26
The Niantic Inn
Bridgehampton Inn
Property grounds

Bridgehampton Inn

3.5 star property
9.4 out of 10, Exceptional, (213)
"Lovely inn, with very accommodating staff. "
The price is CA $424
CA $484 total
includes taxes & fees
Mar 24 - Mar 25
Bridgehampton Inn
Baron's Cove
Front of property - evening/night

Baron's Cove

4.0 star property
9.0 out of 10, Wonderful, (211)
"Perfect get away "
The price is CA $248
CA $312 total
includes taxes & fees
Mar 23 - Mar 24
Baron's Cove
Sag Harbor Inn
Outdoor pool

Sag Harbor Inn

3.5 star property
9.4 out of 10, Exceptional, (500)
"So Good !!!!!!!"
The price is CA $282
CA $322 total
includes taxes & fees
Feb 24 - Feb 25
Sag Harbor Inn
The 1708 House
Exterior

The 1708 House

3.0 star property
The price is CA $348
CA $408 total
includes taxes & fees
Feb 23 - Feb 24
The 1708 House
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.
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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.

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 15 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.