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Find hotels in The Heights, Shelter Island Heights from NT$2,340

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Dec 4 - Dec 5
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Dec 12 - Dec 14

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Discover 3,984 The Heights hotels and places to stay, with room rates, reviews, and availability. Most hotels are fully refundable.

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 NT$5,788
NT$6,612 total
includes taxes & fees
Dec 15 - Dec 16
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 NT$4,106
NT$6,224 total
includes taxes & fees
Dec 29 - Dec 30
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 NT$2,099
NT$2,413 total
includes taxes & fees
Jan 4 - 2026/1/5
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 NT$2,442
NT$2,808 total
includes taxes & fees
Dec 7 - Dec 8
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 NT$3,212
NT$4,152 total
includes taxes & fees
Dec 6 - Dec 7
Hamlet Inn
Indoor pool, open 9:00 AM to 9:00 PM, sun 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 NT$3,167
NT$3,642 total
includes taxes & fees
Dec 14 - Dec 15
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 NT$3,457
NT$3,980 total
includes taxes & fees
Dec 22 - Dec 23
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 NT$2,508
NT$2,884 total
includes taxes & fees
Dec 13 - Dec 14
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 Captain Stannard
Seasonal outdoor pool, pool umbrellas, sun 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 NT$6,094
NT$8,495 total
includes taxes & fees
Jan 4 - 2026/1/5
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 NT$4,763
NT$6,694 total
includes taxes & fees
Dec 7 - Dec 8
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 NT$3,718
NT$4,434 total
includes taxes & fees
Jan 4 - 2026/1/5
Southampton Long Island Hotel
Garden Suite King | Premium bedding, down comforters, individually decorated
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)
"Beautiful"
United States
Linda
The price is NT$5,808
NT$6,635 total
includes taxes & fees
Dec 8 - Dec 9
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 NT$2,102
NT$2,490 total
includes taxes & fees
Dec 11 - Dec 12
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 NT$2,035
NT$2,340 total
includes taxes & fees
Jan 2 - 2026/1/3
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 NT$6,949
NT$7,713 total
includes taxes & fees
Dec 10 - Dec 11
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 NT$8,878
NT$10,144 total
includes taxes & fees
Dec 6 - Dec 7
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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Where to stay in The Heights

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

Hay Beach

Hay Beach might not have many top sights, but Gardiner's Bay Country Club and Greenport Carousel are two attractions nearby that you can check out.

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

Explore a world of travel with Expedia

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 neighborhood has to offer. Be sure to check out 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 guesthouse offers free parking and free WiFi.
How many hotels will I 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 accommodations in The Heights.
If I need to cancel my hotel reservation in The Heights, will I receive a refund?
Yes, most hotel bookings are fully refundable if cancelled prior to the hotel's cancellation deadline, which is usually within 24-48 hours of your scheduled arrival. If you have a reservation that's non-refundable, you may still be able to cancel and get a refund within 24 hours of your booking. Plug in your dates, click on "Search", then use the "fully refundable" filter to get the best options available in The Heights.
Where can I learn more about changing or cancelling my trip to The Heights?
To find more details about picking new dates or cancelling your trip to The Heights, click here.
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.