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Check prices for these dates

Next weekend
9 Oct - 11 Oct
In two weeks
16 Oct - 18 Oct

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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, (65 reviews)
"It’s a beautiful property with a fun bar and delicious restaurant . The rooms were beautiful and the bed was super comfortable"
United States
Kristin
The price is ฿5,009
฿5,722 total
includes taxes & fees
1 Nov - 2 Nov
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, (87 reviews)
"Such a cute place to stay! Bill was super kind and helpful! I was only in for a quick night but I would definitely stay here again!!"
United States
Tracey
The price is ฿6,204
฿7,088 total
includes taxes & fees
2 Nov - 3 Nov
House on Chase Creek
A rooftop terrace with lounge chairs, a wooden table, and a view of the landscape.

3. The Harbor Front Inn

The Harbor Front Inn
3.5 star property
2.4 km from The Heights
9.0 out of 10, Wonderful, (661 reviews)
"Great location"
United States
Jordan
The price is ฿5,406
฿7,135 total
includes taxes & fees
1 Nov - 2 Nov
The Harbor Front Inn
A modern building entrance with a black and white striped awning, a staircase leading inside, and two bicycles parked outside.

4. The Menhaden

The Menhaden
3.5 star property
2.4 km from The Heights
9.6 out of 10, Exceptional, (191 reviews)
"Staff was very accommodating and extremely nice, Great stay!"
United States
Lisa
The price is ฿11,595
฿14,590 total
includes taxes & fees
2 Nov - 3 Nov
The Menhaden
A pathway flanked by lush greenery and bamboo, leading to a building with a wooden exterior.

5. American Beech Hotel

American Beech Hotel
3.5 star property
2.6 km from The Heights
9.0 out of 10, Wonderful, (208 reviews)
"Great location, very friendly and helpful "
United States
Mary
The price is ฿8,417
฿10,958 total
includes taxes & fees
5 Oct - 6 Oct
American Beech Hotel
A two-story house with a balcony, outdoor seating area, and a variety of plants.

6. Zey Hotel

Zey Hotel
3.5 star property
2.7 km from The Heights
9.2 out of 10, Wonderful, (419 reviews)
"Great location…thoroughly enjoyed our time."
United States
Renee
The price is ฿5,663
฿6,470 total
includes taxes & fees
5 Oct - 6 Oct
Zey Hotel
A room with a bed, two wicker chairs with checkered cushions, a small round table with a vase of flowers, and a view of a lake through a window with a bamboo blind.

7. 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, (172 reviews)
"This is a great place that brings you back to a special time. Staff were exceptionally friendly and helpful. Made us feel like we were family - highly recommend."
United States
Keith
The price is ฿10,907
฿12,461 total
includes taxes & fees
12 Oct - 13 Oct
Silver Sands Motel & Beach Bungalows
A hotel room with a bed, pillows, a lamp, a wall art piece, and a nightstand.

8. Oyster Estate

Oyster Estate
4.0 star property
2.5 km from The Heights
9.2 out of 10, Wonderful, (291 reviews)
"Clean, great amenities, and friendly staff!"
United States
Elizabeth
The price is ฿8,725
฿10,994 total
includes taxes & fees
1 Nov - 2 Nov
Oyster Estate
A spacious room with wicker furniture, large windows, and a view of the sea.

9. Sound View Greenport

Sound View Greenport
4.0 star property
3.8 km from The Heights
8.4 out of 10, Very good, (745 reviews)
"Great one night stay."
United States
Irene
The price is ฿6,434
฿8,310 total
includes taxes & fees
2 Nov - 3 Nov
Sound View Greenport
Room

10. Shelter Island House

Shelter Island House
3.5 star property
0.9 km from The Heights
8.4 out of 10, Very good, (66 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 ฿6,754
฿7,716 total
includes taxes & fees
5 Oct - 6 Oct
Shelter Island House
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, (344 reviews)
"Loved everything about our stay!"
United States
Melissa
The price is ฿6,773
฿8,577 total
includes taxes & fees
1 Nov - 2 Nov
The Shoals Suites and Slips
Terrace/patio

12. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
3.5 km from The Heights
9.0 out of 10, Wonderful, (295 reviews)
"Great place!"
United States
Christine
The price is ฿5,672
฿10,204 total
includes taxes & fees
1 Nov - 2 Nov
Cliffside Resort Condominiums
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, (62 reviews)
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
United States
Harold
The price is ฿8,940
฿10,214 total
includes taxes & fees
5 Oct - 6 Oct
North Fork Resort
A waterfront property with a large house, multiple boats docked, and lush greenery.

14. Sag Harbor Inn

Sag Harbor Inn
3.5 star property
10 km from The Heights
9.4 out of 10, Exceptional, (671 reviews)
"Free parking, clean, continental breakfast good quality."
United States
Terri
The price is ฿7,349
฿8,397 total
includes taxes & fees
1 Nov - 2 Nov
Sag Harbor Inn
A pool area with umbrellas, potted plants, and a pathway leading to a building.

15. Faraway Sag Harbor

Faraway Sag Harbor
4.0 star property
10.1 km from The Heights
9.0 out of 10, Wonderful, (310 reviews)
"Excellent hotel. Comfortable beds. Nice decorated. Very professional and friendly staff."
United States
Miguel
The price is ฿13,742
฿17,271 total
includes taxes & fees
2 Nov - 3 Nov
Faraway Sag Harbor
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)
"Front desk helpful! Indoor bar area nice area for single traveler plenty of space."
United States
Toni and Zak
The price is ฿5,260
฿6,628 total
includes taxes & fees
1 Nov - 2 Nov
Water's Edge Resort & Spa
A modern building with a pool, featuring a dining area with tables and chairs, and a glass entrance.

17. Topping Rose House

Topping Rose House
4.5 star property
16.5 km from The Heights
9.0 out of 10, Wonderful, (162 reviews)
"Incredible stay. Going back in the fall"
United States
Adam
The price is ฿20,991
฿24,100 total
includes taxes & fees
5 Oct - 6 Oct
Topping Rose House
A round table with a magazine, a plate with a pastry, a cup, and a vase with flowers.

18. Shorewood Inn

Shorewood Inn
2.5 star property
24.5 km from The Heights
8.4 out of 10, Very good, (824 reviews)
"Clean and friendly"
United States
Heather
The price is ฿2,869
฿3,278 total
includes taxes & fees
5 Oct - 6 Oct
Shorewood Inn
A modern lounge area with a pool view, white furniture, and contemporary lighting fixtures.

19. The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
22.6 km from The Heights
9.6 out of 10, Exceptional, (593 reviews)
"nice room for the price in season"
United States
Frank
The price is ฿4,833
฿5,521 total
includes taxes & fees
12 Oct - 13 Oct
The Bentley Hotel Southampton
A spacious lobby with two sofas, a coffee table, and a flat-screen TV mounted on the wall.

20. 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, (1,001 reviews)
"Convenient location great breakfast"
United States
Amy
The price is ฿3,252
฿3,740 total
includes taxes & fees
1 Nov - 2 Nov
Quality Inn Old Saybrook - Westbrook
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 Gardiner's Bay Country Club and Greenport Carousel, some noteworthy sights in the nearby area.

Top The Heights Hotel Reviews

The Chequit

The Chequit

8/10 Good
"Friendly staff , Unique property."
Patrick 1-night trip
Posted 1 hour ago
The Chequit

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 12 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.