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Find hotels in The Heights, Shelter Island Heights

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Discover 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
$104 nightly
The price is $119
Jan 6 - Jan 7, 2026
Total with taxes and fees
House on Chase Creek
Exterior
Econo Lodge Inn & Suites Old Saybrook Westbrook

Econo Lodge Inn & Suites Old Saybrook Westbrook

2.0 star property
14.5 mi from The Heights
7.2 out of 10, Good, (460)
"🙂"
United States
Jared
$67 nightly
The price is $77
Jan 4 - Jan 5, 2026
Total with taxes and fees
Econo Lodge Inn & Suites Old Saybrook Westbrook
Property grounds
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2.0 star property
14.5 mi from The Heights
8.0 out of 10, Very Good, (1000)
"A welcoming place with some nice touches."
United States
Leslie
$77 nightly
The price is $89
Dec 8 - Dec 9
Total with taxes and fees
Pier Blue Inn Old Saybrook - Essex
Property grounds
Clinton Motel

Clinton Motel

2.5 star property
15.8 mi from The Heights
8.6 out of 10, Excellent, (296)
"Great staff and clean rooms"
United States
Tyler
$78 nightly
The price is $90
Dec 7 - Dec 8
Total with taxes and fees
Clinton Motel
Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas
Hamlet Inn

Hamlet Inn

2.0 star property
14.3 mi from The Heights
8.6 out of 10, Excellent, (440)
"Great weekend stay! staff was super kind and property was beautiful! "
United States
Chyanne
$114 nightly
The price is $128
Dec 7 - Dec 8
Total with taxes and fees
Hamlet Inn
Terrace/patio
Shorewood Inn

Shorewood Inn

2.5 star property
15.2 mi 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
$93 nightly
The price is $106
Dec 21 - Dec 22
Total with taxes and fees
Shorewood Inn
Terrace/patio
The Bentley Hotel Southampton

The Bentley Hotel Southampton

2.0 star property
14.1 mi from The Heights
9.6 out of 10, Exceptional, (390)
"great cost-effective option; room was very spacious and clean."
United States
Isadora
$118 nightly
The price is $135
Dec 11 - Dec 12
Total with taxes and fees
The Bentley Hotel Southampton
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
16.5 mi from The Heights
7.8 out of 10, Good, (1001)
"Staff was kind. Easy, comfortable stay."
United States
Jake
$101 nightly
The price is $116
Dec 14 - Dec 15
Total with taxes and fees
Quality Inn Old Saybrook - Westbrook
One Bedroom Harbor View Terrace Suite | View from room
The Harbor Front Inn

The Harbor Front Inn

3.5 star property
1.5 mi from The Heights
8.8 out of 10, Excellent, (540)
"Awesome stay!!! Great Location "
United States
Bryan
$174 nightly
The price is $199
Dec 29 - Dec 30
Total with taxes and fees
The Harbor Front Inn
Outdoor pool
The Atlantic Hotel

The Atlantic Hotel

2.5 star property
13.8 mi from The Heights
7.2 out of 10, Good, (973)
"Great hotel for a quick stay - very friendly staff"
United States
Dianne
$138 nightly
The price is $158
Dec 20 - Dec 21
Total with taxes and fees
The Atlantic Hotel
Garden Suite King | Premium bedding, down comforters, individually decorated
The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 star property
2.5 mi from The Heights
9.6 out of 10, Exceptional, (226)
"Beautiful"
United States
Linda
$174 nightly
The price is $199
Dec 18 - Dec 19
Total with taxes and fees
The Shoals Suites and Slips
Property grounds
Liberty Inn

Liberty Inn

2.0 star property
16 mi from The Heights
7.4 out of 10, Good, (640)
"Great little place to stay with friendly staff and clean room"
United States
Carolan
$83 nightly
The price is $96
Dec 13 - Dec 14
Total with taxes and fees
Liberty Inn
Desk, free WiFi, bed sheets
Southampton Long Island Hotel

Southampton Long Island Hotel

2.5 star property
13 mi from The Heights
8.6 out of 10, Excellent, (203)
"Good location. Nice people!! "
United States
Theresa
$125 nightly
The price is $142
Jan 5 - Jan 6, 2026
Total with taxes and fees
Southampton Long Island Hotel
Exterior
Lamplighter Motel - Clinton, Connecticut

Lamplighter Motel - Clinton, Connecticut

2.5 star property
15.3 mi from The Heights
6.4 out of 10, (228)
"Would stay again. "
United States
pamela
$65 nightly
The price is $75
Jan 2 - Jan 3, 2026
Total with taxes and fees
Lamplighter Motel - Clinton, Connecticut
Standard Studio, 1 King Bed, Non Smoking | Premium bedding, free WiFi, bed sheets
The Niantic Inn

The Niantic Inn

2.5 star property
18.7 mi from The Heights
9.2 out of 10, Wonderful, (126)
"Easy parking. Walkable dining and to boardwalk. Quaint shopping."
United States
Kerry
$94 nightly
The price is $109
Dec 17 - Dec 18
Total with taxes and fees
The Niantic Inn
Exterior
The Sagaponack

The Sagaponack

3.0 star property
10.6 mi from The Heights
8.8 out of 10, Excellent, (211)
"Clean & amenities, staff friendly Thank you "
United States
Archil
$176 nightly
The price is $202
Dec 15 - Dec 16
Total with taxes and fees
The Sagaponack
IPod dock, MP3 dock
The Captain Stannard

The Captain Stannard

3.0 star property
14.9 mi 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
$206 nightly
The price is $229
Dec 11 - Dec 12
Total with taxes and fees
The Captain Stannard
Seasonal outdoor pool, pool umbrellas, sun loungers
Sound View Greenport

Sound View Greenport

4.0 star property
2.4 mi from The Heights
8.6 out of 10, Excellent, (597)
"Staff was amazing , room clean view phenomenal "
United States
Denise
$237 nightly
The price is $271
Jan 6 - Jan 7, 2026
Total with taxes and fees
Sound View Greenport
Property amenity
Super 8 by Wyndham Old Saybrook

Super 8 by Wyndham Old Saybrook

2.0 star property
14.7 mi from The Heights
7.0 out of 10, Good, (907)
"A simple, affordable, conveniently located, and pleasant stay."
United States
Jason
$70 nightly
The price is $80
Dec 8 - Dec 9
Total with taxes and fees
Super 8 by Wyndham Old Saybrook
Property grounds
The Hampton Maid

The Hampton Maid

2.5 star property
15.4 mi from The Heights
9.0 out of 10, Wonderful, (688)
"Great place to stay"
United States
Mitchell
$188 nightly
The price is $215
Dec 22 - Dec 23
Total with taxes and fees
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 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 3 days ago
The Niantic Inn

Frequently asked questions

What are the best hotels in The Heights that travelers recommend?
The Chequit stands out as a top choice in Shelter Island Heights, boasting an impressive traveler review score of 8.8. This charming hotel combines a rustic vibe with modern comforts, making it an inviting retreat for all types of travelers. Guests love its premium bedding and Frette Italian sheets, ensuring a restful night's sleep after a day of adventure. With free Wi-Fi and free self-parking, convenience is at the forefront of your stay, allowing you to focus on enjoying everything the area has to offer.
What are the best family hotels in The Heights?
The Chequit, located in the charming Shelter Island Heights, is an inviting family-friendly hotel that promises a delightful stay for guests of all ages. Rated 8.8 by travelers, this property offers connecting rooms, making it easier for families to stay close together while enjoying their own space.
What are the best budget hotels in The Heights?
The Chequit, located in the charming Shelter Island Heights, is a delightful option for budget-conscious travelers seeking a cozy retreat. With an excellent review score of 8.8, this hotel boasts free WiFi in rooms, ensuring you stay connected during your getaway, and premium bedding with Frette Italian sheets for a luxurious night's sleep.
Can I cancel my hotel reservation on Expedia?
Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline – this is often within 24-48 hours of your scheduled arrival. If you have a non-refundable booking, it might still be possible to receive a refund if you cancel it within 24 hours of booking. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use our "Fully refundable property" filter during your search to find the right The Heights hotel for you.
How can I save on a The Heights hotel booking with Expedia?
With Expedia, you earn OneKeyCash™* on eligible The Heights hotel bookings for every dollar you spend – just join our One Key™ travel rewards program to get started. It's free to join, and you'll unlock our lowest Member Prices as soon as you're signed in. On top of this, you could also save significantly by bundling your hotel and flights together on Expedia.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
How much is the nightly rate at a The Heights hotel?
Hotel prices in The Heights often vary, but you can find a great deal on Expedia. Different factors affect nightly hotel rates, such as the time of year or the days of the week you want to book. To find the best deals for your stay, be flexible with your dates, and sort search results by "Price: low to high" for our cheapest rates.

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