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Shelter Island Heights Hotel Guide. Hotels in The Heights, Shelter Island Heights, United States of America

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14 Dec - 15 Dec
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15 Dec - 16 Dec
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19 Dec - 21 Dec
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26 Dec - 28 Dec

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Our top choices for The Heights hotels

View from property
House on Chase Creek

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 €101
includes taxes & fees
6 Jan - 7 Jan 2026
House on Chase Creek
Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas
Hamlet Inn

Hamlet Inn

Hamlet Inn
2.0 star property
23.1 km from The Heights
8.6 out of 10, Excellent, (441)
"Great weekend stay! staff was super kind and property was beautiful! "
United States
Chyanne
The price is €98
includes taxes & fees
15 Dec - 16 Dec
Hamlet Inn
Terrace/patio
The Bentley Hotel Southampton

The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
22.6 km from The Heights
9.6 out of 10, Exceptional, (394)
"great cost-effective option; room was very spacious and clean."
United States
Isadora
The price is €123
includes taxes & fees
21 Dec - 22 Dec
The Bentley Hotel Southampton
One Bedroom Harbor View Terrace Suite | View from room
The Harbor Front Inn

The Harbor Front Inn

The Harbor Front Inn
3.5 star property
2.4 km from The Heights
8.8 out of 10, Excellent, (547)
"Awesome stay!!! Great Location "
United States
Bryan
The price is €172
includes taxes & fees
15 Dec - 16 Dec
The Harbor Front Inn
Standard Studio, 1 King Bed, Non Smoking
The Niantic Inn

The Niantic Inn

The Niantic Inn
2.5 star property
30.1 km from The Heights
9.2 out of 10, Wonderful, (128)
"Easy parking. Walkable dining and to boardwalk. Quaint shopping."
United States
Kerry
The price is €79
includes taxes & fees
23 Dec - 24 Dec
The Niantic Inn
Garden Suite King
The Shoals Suites and Slips

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, (228)
"Food!"
United States
Ryan
The price is €181
includes taxes & fees
15 Dec - 16 Dec
The Shoals Suites and Slips
Terrace/patio
Shorewood Inn

Shorewood Inn

Shorewood Inn
2.5 star property
24.5 km from The Heights
8.6 out of 10, Excellent, (709)
"Couldn't have been easier! The woman at the front desk was warm and welcoming, the room was super clean and cute with the heat turned on full blast in anticipation of my arrival. Adorable backyard with seating, too. Super hot water in the shower. Perfect for an impromptu winter getaway. "
United States
Mahlon
Shorewood Inn
Property grounds
Clinton Motel

Clinton Motel

Clinton Motel
2.5 star property
25.4 km from The Heights
8.6 out of 10, Excellent, (297)
"Great staff and clean rooms"
United States
Tyler
The price is €76
includes taxes & fees
4 Jan - 5 Jan 2026
Clinton Motel
Property grounds
Pier Blue Inn Old Saybrook - Essex

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, (1002)
"A welcoming place with some nice touches."
United States
Leslie
Pier Blue Inn Old Saybrook - Essex
Seasonal outdoor pool, pool umbrellas, pool loungers
Sound View Greenport

Sound View Greenport

Sound View Greenport
4.0 star property
3.8 km from The Heights
8.6 out of 10, Excellent, (598)
"Staff was amazing , room clean view phenomenal "
United States
Denise
The price is €206
includes taxes & fees
13 Jan - 14 Jan 2026
Sound View Greenport
Exterior
Econo Lodge Inn & Suites Old Saybrook Westbrook

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 €66
includes taxes & fees
4 Jan - 5 Jan 2026
Econo Lodge Inn & Suites Old Saybrook Westbrook
Indoor pool, open 9:00 AM to 9:00 PM, pool loungers
Quality Inn Old Saybrook - Westbrook

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, (1002)
"Staff was kind. Easy, comfortable stay."
United States
Jake
The price is €99
includes taxes & fees
21 Dec - 22 Dec
Quality Inn Old Saybrook - Westbrook
Outdoor pool
The Atlantic Hotel

The Atlantic Hotel

The Atlantic Hotel
2.5 star property
22.1 km from The Heights
7.2 out of 10, Good, (974)
"Great hotel for a quick stay - very friendly staff"
United States
Dianne
The Atlantic Hotel
Exterior
Zey Hotel

Zey Hotel

Zey Hotel
3.5 star property
2.7 km from The Heights
9.2 out of 10, Wonderful, (290)
"Loved this place. Lots of places to relax and play games. Super-friendly staff. Can't wait to go back b"
United States
Susie
Zey Hotel
Exterior
The Sagaponack

The Sagaponack

The Sagaponack
3.0 star property
17.1 km from The Heights
8.8 out of 10, Excellent, (213)
"Clean & amenities, staff friendly Thank you "
United States
Archil
The price is €182
includes taxes & fees
15 Dec - 16 Dec
The Sagaponack
Desk, free WiFi, bed sheets
Southampton Long Island Hotel

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 €121
includes taxes & fees
13 Jan - 14 Jan 2026
Southampton Long Island Hotel
Exterior
Aqua by American Beech - Adults Only

Aqua by American Beech - Adults Only

Aqua by American Beech - Adults Only
2.5 star property
26 km from The Heights
9.4 out of 10, Exceptional, (312)
"Relaxing stay"
United States
Kristin
Aqua by American Beech - Adults Only
Exterior
American Beech Hotel

American Beech Hotel

American Beech Hotel
3.5 star property
2.6 km from The Heights
8.8 out of 10, Excellent, (195)
"The property was clean beautiful and pleasant. Loved the trendy decor."
United States
Jennifer
The price is €208
includes taxes & fees
21 Dec - 22 Dec
American Beech Hotel
Beach bar
Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
2.3 km from The Heights
9.8 out of 10, Exceptional, (142)
"Great get away "
United States
Charles
Silver Sands Motel & Beach Bungalows
Property grounds
The Hampton Maid

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 Hampton Maid
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.

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

Madison Beach Hotel

Madison Beach Hotel

10/10 Excellent
"Great overall service."
Richard T 3-night trip
Posted 2 days ago
Madison Beach Hotel

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 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.