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Aug 28 - Aug 30
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Sep 4 - Sep 6

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Our top choices for The Heights hotels

An outdoor patio area with string lights, tables, chairs, and a fire pit.

1. The Chequit

The Chequit
3.0 star property
The Heights
9.2 out of 10, Wonderful, (52 reviews)
"Everything was great ! Wish we had been there when restaurant was open."
United States
Kathleen
The price is ￥46,587
￥53,224 total
includes taxes & fees
Sep 8 - Sep 9
The Chequit
A serene landscape with a calm body of water reflecting trees with autumn foliage.

2. House on Chase Creek

House on Chase Creek
2.5 star property
The Heights
9.4 out of 10, Exceptional, (86 reviews)
"Nice owner.. convenient location"
United States
Calvin
The price is ￥39,115
￥44,689 total
includes taxes & fees
Sep 9 - Sep 10
House on Chase Creek
A deck with outdoor seating, overlooking a body of water with a sunset view.

3. The Pridwin Hotel

The Pridwin Hotel
4.0 star property
2 km from The Heights
9.4 out of 10, Exceptional, (112 reviews)
"Stunning hotel! Will def stay again!"
United States
Anna
The price is ￥85,461
￥107,403 total
includes taxes & fees
Sep 13 - Sep 14
The Pridwin Hotel

4. Shelter Island House

Shelter Island House
3.5 star property
0.9 km from The Heights
8.4 out of 10, Very Good, (64 reviews)
"This boutique hotel is a true gem. Set among lush trees and beautiful landscaping, and with excellent indoor space, it provides a welcoming and relaxing atmosphere."
United States
Dorothy
The price is ￥50,347
￥57,522 total
includes taxes & fees
Sep 2 - Sep 3
Shelter Island House
A modern building entrance with a black and white striped awning, a staircase leading inside, and two bicycles parked outside.

5. The Menhaden

The Menhaden
3.5 star property
2.4 km from The Heights
9.6 out of 10, Exceptional, (189 reviews)
"Staff was very accommodating and extremely nice, Great stay!"
United States
Lisa
The price is ￥72,742
￥89,478 total
includes taxes & fees
Aug 30 - Aug 31
The Menhaden
A bedroom with a bed, bedside tables, a lamp, a window, and a door.

6. West Neck Guesthouse

West Neck Guesthouse
3.5 star property
0.6 km from The Heights
8.2 out of 10, Very Good, (46 reviews)
"It was great! The location was perfect, plenty of amenities close by as well. Easy ferry access depending on time of day. Room was very clean. Will be staying again!"
United States
Allie
The price is ￥49,909
￥57,022 total
includes taxes & fees
Sep 1 - Sep 2
West Neck Guesthouse
A rooftop terrace with lounge chairs, a wooden table, and a view of the landscape.

7. The Harbor Front Inn

The Harbor Front Inn
3.5 star property
2.4 km from The Heights
8.8 out of 10, Excellent, (641 reviews)
"Overall great stay! People are fantastic!"
United States
John
The price is ￥40,479
￥54,435 total
includes taxes & fees
Sep 8 - Sep 9
The Harbor Front Inn
A two-story house with a balcony, outdoor seating area, and a variety of plants.

8. Zey Hotel

Zey Hotel
3.5 star property
2.7 km from The Heights
9.2 out of 10, Wonderful, (387 reviews)
"Very excellent boutique hotel right on Main st. Beautiful garden for relaxing. Perfect location, friendly staff"
United States
shaun
The price is ￥32,238
￥36,832 total
includes taxes & fees
Sep 1 - Sep 2
Zey Hotel
A seaside dining area with tables, chairs, and umbrellas, overlooking a body of water.

9. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
2.3 km from The Heights
10.0 out of 10, Exceptional, (163 reviews)
"This was my first time in the North fork and this hotel was a total surprise It was absolutely wonderful The accommodations the service the food everything was a delight and we cannot wait to come back"
United States
Sol
The price is ￥57,224
￥65,378 total
includes taxes & fees
Sep 21 - Sep 22
Silver Sands Motel & Beach Bungalows
A cozy living room with a wooden floor, a round dining table, a sofa, and a bookshelf.

10. Oyster Estate

Oyster Estate
4.0 star property
2.5 km from The Heights
9.2 out of 10, Wonderful, (284 reviews)
"Great location, great hotel, great staff! "
United States
Jenny
The price is ￥47,696
￥60,093 total
includes taxes & fees
Sep 8 - Sep 9
Oyster Estate
A modern outdoor seating area with two wicker chairs and a small table, overlooking a body of water and a wooden deck.

11. The Shoals Suites and Slips

The Shoals Suites and Slips
3.5 star property
4 km from The Heights
9.4 out of 10, Exceptional, (327 reviews)
"Amazing stay!!!"
United States
Maria
The price is ￥46,294
￥56,871 total
includes taxes & fees
Sep 2 - Sep 3
The Shoals Suites and Slips
A pathway flanked by lush greenery and bamboo, leading to a building with a wooden exterior.

12. American Beech Hotel

American Beech Hotel
3.5 star property
2.6 km from The Heights
9.0 out of 10, Wonderful, (206 reviews)
"The hotel doesn’t reception doesn’t open till 9am. For early risers we had to leave the hotel just to get coffee. 9am is unheard of for a hotel"
United States
kerri
The price is ￥59,031
￥73,810 total
includes taxes & fees
Sep 9 - Sep 10
American Beech Hotel
A modern house with a deck, outdoor seating, and a fire pit.

13. North Fork Resort

North Fork Resort
3.0 star property
3.4 km from The Heights
9.6 out of 10, Exceptional, (50 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"
United States
Lisa
The price is ￥48,878
￥55,842 total
includes taxes & fees
Sep 13 - Sep 14
North Fork Resort
A spacious room with wicker furniture, large windows, and a view of the sea.

14. Sound View Greenport

Sound View Greenport
4.0 star property
3.8 km from The Heights
8.4 out of 10, Very Good, (706 reviews)
"Beautiful location! Everything was excellent!"
United States
Suzanne
The price is ￥36,725
￥55,600 total
includes taxes & fees
Sep 15 - Sep 16
Sound View Greenport

15. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
3.5 km from The Heights
9.0 out of 10, Wonderful, (289 reviews)
"Great place!"
United States
Christine
The price is ￥48,083
￥69,126 total
includes taxes & fees
Sep 21 - Sep 22
Cliffside Resort Condominiums
A spacious lobby with two sofas, a coffee table, and a flat-screen TV mounted on the wall.

16. Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
26.5 km from The Heights
7.8 out of 10, Good, (1,000 reviews)
"staff is friendly and helpful breakfast had many options room was clean"
United States
Theresa
The price is ￥16,110
￥18,527 total
includes taxes & fees
Sep 20 - Sep 21
Quality Inn Old Saybrook - Westbrook
A sign for Pier Blue Guesthouse with a logo and name.

17. Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex
2.0 star property
23.3 km from The Heights
8.0 out of 10, Very Good, (1,001 reviews)
"It was a very nice hotel. The room was clean and comfortable, the staff was friendly, and the location was convenient. We had a great stay and really enjoyed our time there."
United States
Egor
The price is ￥13,211
￥15,192 total
includes taxes & fees
Aug 30 - Aug 31
Pier Blue Inn Old Saybrook - Essex
A waterfront property with a large house, multiple boats docked, and lush greenery.

18. Sag Harbor Inn

Sag Harbor Inn
3.5 star property
10 km from The Heights
9.4 out of 10, Exceptional, (660 reviews)
"Everything about the place was great - great value overlooking the Harbor!"
United States
Christopher
The price is ￥56,357
￥64,389 total
includes taxes & fees
Sep 20 - Sep 21
Sag Harbor Inn
A parking lot with a building in the background.

19. Clinton Motel

Clinton Motel
2.5 star property
25.4 km from The Heights
8.6 out of 10, Excellent, (333 reviews)
"Hotel was clean and the staff was pleasant. The pool was wonderful! I would stay there again."
United States
Selena
The price is ￥12,577
￥14,464 total
includes taxes & fees
Sep 3 - Sep 4
Clinton Motel
A two-story house with a steeply pitched roof, green shutters, and a brick entrance.

20. Head of Pond House

Head of Pond House
3.0 star property
18.3 km from The Heights
10.0 out of 10, Exceptional, (13 reviews)
"What a wonderful little gem in the heart of Watermill. This was our favorite Hamptons B&B stay and we can’t wait to comeback!"
United States
Liz
The price is ￥335,275
￥383,051 total
includes taxes & fees
Sep 9 - Sep 10
Head of Pond 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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Where to stay in The Heights

Find the best The Heights areas and neighborhoods for the activities you enjoy most.
A calm lake with reflections of clouds, surrounded by trees and a distant structure.

Hay Beach

Hay Beach might not have many top sights, but Gardiner's Bay Country Club and Greenport Carousel are two attractions nearby that you can check out.

Top The Heights Hotel Reviews

Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"Just an outstanding hotel in a breathtakingly beautiful setting!! I couldn’t be more impressed & look forward to returning! 10 stars!!"
Joan 2-night trip
Posted 18 hours ago
Water's Edge Resort & Spa

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 our traveler data, The Chequit is one of the top choices for your stay in The Heights. This hotel offers a restaurant and free parking.
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 11 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.