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The Heights Hotels, Shelter Island Heights

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4 Dec - 5 Dec
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5 Dec - 6 Dec
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5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

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

View from property
House on Chase Creek

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
One Bedroom Harbor View Terrace Suite | View from room
The Harbor Front Inn

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
Exterior
Econo Lodge Inn & Suites Old Saybrook Westbrook

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
Terrace/patio
Shorewood Inn

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
Property grounds
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, (1000)
"A welcoming place with some nice touches."
United States
Leslie
Pier Blue Inn Old Saybrook - Essex
Property grounds
Clinton Motel

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
Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas
Hamlet Inn

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
Indoor pool, open 9:00 AM to 9:00 PM, pool loungers
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, (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
Terrace/patio
The Bentley Hotel Southampton

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
Property grounds
Liberty Inn

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
IPod dock, MP3 dock
The Captain Stannard

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
Seasonal outdoor pool, pool umbrellas, pool loungers
Sound View Greenport

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
Exterior
The Sagaponack

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
Desk, free WiFi, bed sheets
Southampton Long Island Hotel

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
Garden Suite King
The Shoals Suites and Slips

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
Property amenity
Super 8 by Wyndham Old Saybrook

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
Exterior
Lamplighter Motel - Clinton, Connecticut

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
Terrace/patio
Westbrook Inn B&B

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
Property grounds
The Hampton Maid

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
Outdoor pool
The Atlantic Hotel

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.
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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

The Niantic Inn

The Niantic Inn

10/10 Excellent
"Very friendly staff, incredibly clean & quiet and great location!"
Amanda 1-night trip
Posted 2 days ago
The Niantic Inn

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.