The Best Hotels in The Heights, Shelter Island Heights - 2026 Updated Prices

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Compare popular hotels in The Heights

Property	Property class	Guest rating
The Chequit	3.0 star property	9.0 Wonderful 74 reviews	View
House on Chase Creek	2.5 star property	9.4 Exceptional 87 reviews	View
The Harbor Front Inn	3.5 star property	9.0 Wonderful 669 reviews	View
Silver Sands Motel & Beach Bungalows	4.0 star property	10.0 Exceptional 185 reviews	View
Zey Hotel	3.5 star property	9.2 Wonderful 440 reviews	View

Hotels recommended for families in The Heights

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

The Chequit

The Heights

฿6,984 total

includes taxes & fees

19 Nov - 20 Nov

Where to stay in The Heights

Find the best The Heights areas for the activities you enjoy most.

Hay Beach

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.

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Top The Heights Hotel Reviews

The Harbor Front Inn

10/10 Excellent

"Such a lovely place for a getaway. Charming town and lovely water views!"

Zey Hotel

10/10 Excellent

"The stay was perfect. I can't think of a single thing to criticize. As an example, when we were checking out, we called the manager on his cell to alert him that a fire truck was flushing the street hydrants, and that we noticed that the water in the room was brown. We knew that the maintenance of the hydrants was causing the dirty water. The manager promptly told us we could stay until 6:00 pm for free, so that we would be able to take clean showers. We told him that we had showered early, and that we had no problem. But his response showed how he cared for the guests."

Faraway Sag Harbor

8/10 Good

"Beautiful and charming hotel! Unfortunately the restaurant was only serving breakfast and not dinner, since we arrived off- season. However the restaurant was freezing due to the heating system not working so we had to go elsewhere in town for breakfast. Too bad because it was a lovely room with a harbor view. Our biggest disappointment by far was the coffee in the room and in the lobby. Nasty stuff! I have never tasted coffee this bad in any hotel (and we have been to many). First of all at this high- end price point per night, Faraway should be providing at least a Nespresso machine in each room for a decent morning cup of coffee instead of instant coffee packets which went out with Sanka like forty years ago. :( Then we thought that maybe the coffee urns on the bar in the common area would at least provide a half decent cup of coffee. Boy were we wrong! The fact that other filled cups of coffee which were left on the bar still full told us that other guests felt the same about the quality of coffee. Thank goodness for Goldbergs Bagel shop in town! Come on guys. If you want to be recognized as a high end getaway in an extremely wealthy part of Long Island, please find yourselves a better quality coffee source. Its not that hard these days. We speak for all true coffee lovers."

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.

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Our top choices for The Heights hotels

1. The Chequit

2. House on Chase Creek

3. The Harbor Front Inn

4. Oyster Estate

5. Zey Hotel

6. The Menhaden

7. Silver Sands Motel & Beach Bungalows

8. American Beech Hotel

9. Sound View Greenport

10. The Shoals Suites and Slips

11. Cliffside Resort Condominiums

12. North Fork Resort

13. Shelter Island House

14. Sag Harbor Inn

15. Faraway Sag Harbor

16. The Sagaponack

17. Water's Edge Resort & Spa

18. Topping Rose House

19. Quality Inn Old Saybrook - Westbrook

20. East Hampton House Resort