Photo by Erisa Dilo

The Heights Hotels, Shelter Island Heights

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Filter by

Guest rating
Guest rating
Star rating

3987 Cheap Hotels in The Heights - Specials, Reviews, & Last Minute Deals

House on Chase Creek

2.5 star property
The Heights
9.4 out of 10, Exceptional, (79)
" This was my husband and my first time visiting Shelter Island and I feel lucky that my stay was at the House of ChaseCreek. Bill was excellent in helping us navigate our stay on the Island which made for an enjoyable experience. The house was charming , very clean , and had easy access to the town restaurant s, and Ferry. Highly recommend ! "
United States
Maureen
The price is AU$320
includes taxes & fees
8 Dec - 9 Dec
House on Chase Creek

The Harbor Front Inn

3.5 star property
2.4 km from The Heights
8.8 out of 10, Excellent, (540)
"Awesome stay!!! Great Location "
United States
Bryan
The price is AU$256
includes taxes & fees
29 Dec - 30 Dec
The Harbor Front Inn

Econo Lodge Inn & Suites Old Saybrook Westbrook

2.0 star property
23.3 km from The Heights
7.2 out of 10, Good, (460)
"🙂"
United States
Jared
The price is AU$117
includes taxes & fees
10 Dec - 11 Dec
Econo Lodge Inn & Suites Old Saybrook Westbrook

Shorewood Inn

2.5 star property
24.5 km from The Heights
8.4 out of 10, Very good, (707)
"Bed was very comfortable.. staff was very friendly.. loud traffic in AM.. good water pressure.. would stay here again. "
United States
Shelly
Shorewood Inn

Pier Blue Inn Old Saybrook - Essex

2.0 star property
23.3 km from The Heights
8.0 out of 10, Very good, (1000)
"A welcoming place with some nice touches."
United States
Leslie
Pier Blue Inn Old Saybrook - Essex

Clinton Motel

2.5 star property
25.4 km from The Heights
8.6 out of 10, Excellent, (296)
"Great staff and clean rooms"
United States
Tyler
The price is AU$136
includes taxes & fees
7 Dec - 8 Dec
Clinton Motel

Hamlet Inn

2.0 star property
23.1 km from The Heights
8.6 out of 10, Excellent, (439)
"Great weekend stay! staff was super kind and property was beautiful! "
United States
Chyanne
The price is AU$192
includes taxes & fees
5 Dec - 6 Dec
Hamlet Inn

Quality Inn Old Saybrook - Westbrook

2.5 star property
26.5 km from The Heights
7.8 out of 10, Good, (1001)
"Staff was kind. Easy, comfortable stay."
United States
Jake
The price is AU$176
includes taxes & fees
10 Dec - 11 Dec
Quality Inn Old Saybrook - Westbrook

The Bentley Hotel Southampton

2.0 star property
22.6 km from The Heights
9.6 out of 10, Exceptional, (390)
"great cost-effective option; room was very spacious and clean."
United States
Isadora
The price is AU$192
includes taxes & fees
22 Dec - 23 Dec
The Bentley Hotel Southampton

Liberty Inn

2.0 star property
25.8 km from The Heights
7.4 out of 10, Good, (640)
"Great little place to stay with friendly staff and clean room"
United States
Carolan
The price is AU$127
includes taxes & fees
6 Dec - 7 Dec
Liberty Inn

The Captain Stannard

3.0 star property
24 km from The Heights
9.8 out of 10, Exceptional, (257)
"Amazing stay! Everything was perfect and it is clear that the owners love their jobs and their inn. Can't wait to go back! "
United States
Julie
The price is AU$277
includes taxes & fees
7 Dec - 8 Dec
The Captain Stannard

Sound View Greenport

4.0 star property
3.8 km from The Heights
8.6 out of 10, Excellent, (596)
"Staff was amazing , room clean view phenomenal "
United States
Denise
The price is AU$351
includes taxes & fees
7 Dec - 8 Dec
Sound View Greenport

The Sagaponack

3.0 star property
17.1 km from The Heights
8.8 out of 10, Excellent, (211)
"Clean & amenities, staff friendly Thank you "
United States
Archil
The price is AU$313
includes taxes & fees
7 Dec - 8 Dec
The Sagaponack

Southampton Long Island Hotel

2.5 star property
20.9 km from The Heights
8.6 out of 10, Excellent, (203)
"Good location. Nice people!! "
United States
Theresa
The price is AU$214
includes taxes & fees
2 Jan - 3 Jan 2026
Southampton Long Island Hotel

The Shoals Suites and Slips

3.5 star property
4 km from The Heights
9.6 out of 10, Exceptional, (225)
"Great quick stay"
United States
Jasmine T
The price is AU$295
includes taxes & fees
14 Dec - 15 Dec
The Shoals Suites and Slips

Super 8 by Wyndham Old Saybrook

2.0 star property
23.7 km from The Heights
7.0 out of 10, Good, (906)
"A simple, affordable, conveniently located, and pleasant stay."
United States
Jason
The price is AU$120
includes taxes & fees
7 Dec - 8 Dec
Super 8 by Wyndham Old Saybrook

Lamplighter Motel - Clinton, Connecticut

2.5 star property
24.6 km from The Heights
6.4 out of 10, (228)
"Would stay again. "
United States
pamela
The price is AU$113
includes taxes & fees
2 Jan - 3 Jan 2026
Lamplighter Motel - Clinton, Connecticut

Westbrook Inn B&B

3.0 star property
24 km from The Heights
9.8 out of 10, Exceptional, (175)
"Charming, beautiful inn; excellent food and service."
United States
Michael
The price is AU$243
includes taxes & fees
9 Dec - 10 Dec
Westbrook Inn B&B

The Hampton Maid

2.5 star property
24.7 km from The Heights
9.0 out of 10, Wonderful, (688)
"Great place to stay"
United States
Mitchell
The price is AU$490
includes taxes & fees
5 Dec - 6 Dec
The Hampton Maid

The Atlantic Hotel

2.5 star property
22.1 km from The Heights
7.2 out of 10, Good, (973)
"Great hotel for a quick stay - very friendly staff"
United States
Dianne
The Atlantic Hotel
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.

Our guide on where to stay in The Heights

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

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

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 Expedia customer reviews, House on Chase Creek is the highest ranked property in The Heights. This guest house offers free parking and free WiFi.
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 13 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.