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Check prices for these dates

Next weekend
4 Sept - 6 Sept
In two weeks
11 Sept - 13 Sept

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Our top choices for The Heights hotels

A serene landscape with a calm body of water reflecting trees with autumn foliage.

1. 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 Rp4.347.170
Rp4.966.602 total
includes taxes & fees
8 Sept - 9 Sept
House on Chase Creek
An outdoor patio area with string lights, tables, chairs, and a fire pit.

2. 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 Rp5.175.202
Rp5.912.669 total
includes taxes & fees
8 Sept - 9 Sept
The Chequit

3. 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 Rp5.595.411
Rp6.392.835 total
includes taxes & fees
1 Sept - 2 Sept
Shelter Island House
A bedroom with a bed, bedside tables, a lamp, a window, and a door.

4. 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 Rp5.546.756
Rp6.337.279 total
includes taxes & fees
31 Aug - 1 Sept
West Neck Guesthouse
A rooftop terrace with lounge chairs, a wooden table, and a view of the landscape.

5. The Harbor Front Inn

The Harbor Front Inn
3.5 star property
2.4 km from The Heights
8.8 out of 10, Excellent, (643 reviews)
"Overall great stay! People are fantastic!"
United States
John
The price is Rp4.887.691
Rp6.493.784 total
includes taxes & fees
8 Sept - 9 Sept
The Harbor Front Inn
A seaside dining area with tables, chairs, and umbrellas, overlooking a body of water.

6. 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 Rp6.988.735
Rp7.984.674 total
includes taxes & fees
21 Sept - 22 Sept
Silver Sands Motel & Beach Bungalows
A deck with outdoor seating, overlooking a body of water with a sunset view.

7. 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 Rp9.497.769
Rp11.936.313 total
includes taxes & fees
13 Sept - 14 Sept
The Pridwin Hotel
A cozy living room with a wooden floor, a round dining table, a sofa, and a bookshelf.

8. 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 Rp5.759.071
Rp7.256.142 total
includes taxes & fees
7 Sept - 8 Sept
Oyster Estate
A modern building entrance with a black and white striped awning, a staircase leading inside, and two bicycles parked outside.

9. 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 Rp7.769.350
Rp9.584.121 total
includes taxes & fees
31 Aug - 1 Sept
The Menhaden
A two-story house with a balcony, outdoor seating area, and a variety of plants.

10. Zey Hotel

Zey Hotel
3.5 star property
2.7 km from The Heights
9.2 out of 10, Wonderful, (389 reviews)
"Very excellent boutique hotel right on Main st. Beautiful garden for relaxing. Perfect location, friendly staff"
United States
shaun
The price is Rp3.582.832
Rp4.093.386 total
includes taxes & fees
1 Sept - 2 Sept
Zey Hotel
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, (330 reviews)
"Amazing stay!!!"
United States
Maria
The price is Rp5.144.947
Rp6.320.426 total
includes taxes & fees
1 Sept - 2 Sept
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 Rp6.560.564
Rp8.203.006 total
includes taxes & fees
8 Sept - 9 Sept
American Beech Hotel

13. 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 Rp5.343.817
Rp7.682.478 total
includes taxes & fees
21 Sept - 22 Sept
Cliffside Resort Condominiums
A spacious lobby with two sofas, a coffee table, and a flat-screen TV mounted on the wall.

14. 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, (1,002 reviews)
"staff is friendly and helpful breakfast had many options room was clean"
United States
Theresa
The price is Rp1.789.647
Rp2.058.094 total
includes taxes & fees
20 Sept - 21 Sept
Quality Inn Old Saybrook - Westbrook
A sign for Pier Blue Guesthouse with a logo and name.

15. 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, (1,002 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 Rp1.599.605
Rp1.839.545 total
includes taxes & fees
31 Aug - 1 Sept
Pier Blue Inn Old Saybrook - Essex
A large hotel with a spacious outdoor patio area, multiple dining tables, and umbrellas.

16. Water's Edge Resort & Spa

Water's Edge Resort & Spa
3.5 star property
23.3 km from The Heights
8.8 out of 10, Excellent, (1,000 reviews)
"Great staff Multiple food and drink options"
United States
Thomas
The price is Rp4.124.238
Rp5.048.078 total
includes taxes & fees
14 Sept - 15 Sept
Water's Edge Resort & Spa
A waterfront property with a large house, multiple boats docked, and lush greenery.

17. Sag Harbor Inn

Sag Harbor Inn
3.5 star property
10 km from The Heights
9.4 out of 10, Exceptional, (662 reviews)
"Location and scenery"
United States
Loretta
The price is Rp6.263.322
Rp7.155.847 total
includes taxes & fees
20 Sept - 21 Sept
Sag Harbor Inn
A spacious room with wicker furniture, large windows, and a view of the sea.

18. Sound View Greenport

Sound View Greenport
4.0 star property
3.8 km from The Heights
8.4 out of 10, Very good, (710 reviews)
"Great one night stay."
United States
Irene
The price is Rp5.188.472
Rp7.443.942 total
includes taxes & fees
15 Sept - 16 Sept
Sound View Greenport
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 Rp1.397.747
Rp1.607.409 total
includes taxes & fees
31 Aug - 1 Sept
Clinton Motel
A living room with a stone fireplace, grey sofas, and a coffee table.

20. The Captain Stannard

The Captain Stannard
3.0 star property
24 km from The Heights
9.8 out of 10, Exceptional, (281 reviews)
"Had a great stay. Everything was fantastic."
United States
Deborah
The price is Rp4.138.729
Rp4.593.989 total
includes taxes & fees
31 Aug - 1 Sept
The Captain Stannard
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 for the activities you enjoy most.
A calm lake with reflections of clouds, surrounded by trees and a distant structure.

Hay Beach

When in Hay Beach, you can plan a visit to Greenport Carousel and Greenport Harbor Brewing Company, some noteworthy sights in the nearby area.

Top The Heights Hotel Reviews

Sound View Greenport

Sound View Greenport

10/10 Excellent
"Loved the location!"
Jessica 1-night trip
Posted 5 hours ago
Sound View Greenport

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 our traveller 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 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 11 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.