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Find hotels in The Heights, Shelter Island Heights

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Our top choices for The Heights hotels

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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
$104 nightly
The price is $119
Jan 7 - Jan 8, 2026
Total with taxes and fees
House on Chase Creek
Golf
Hamlet Inn

Hamlet Inn

Hamlet Inn
2.0 star property
14.3 mi from The Heights
8.6 out of 10, Excellent, (441)
"Great weekend stay! staff was super kind and property was beautiful! "
United States
Chyanne
$114 nightly
The price is $128
Dec 14 - Dec 15
Total with taxes and fees
Hamlet Inn
Reception
The Bentley Hotel Southampton

The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
14.1 mi from The Heights
9.6 out of 10, Exceptional, (394)
"great cost-effective option; room was very spacious and clean."
United States
Isadora
$118 nightly
The price is $135
Dec 22 - Dec 23
Total with taxes and fees
The Bentley Hotel Southampton
Lobby lounge
The Harbor Front Inn

The Harbor Front Inn

The Harbor Front Inn
3.5 star property
1.5 mi from The Heights
8.8 out of 10, Excellent, (546)
"Awesome stay!!! Great Location "
United States
Bryan
$174 nightly
The price is $198
Jan 5 - Jan 6, 2026
Total with taxes and fees
The Harbor Front Inn
Beach nearby
The Niantic Inn

The Niantic Inn

The Niantic Inn
2.5 star property
18.7 mi from The Heights
9.2 out of 10, Wonderful, (127)
"Easy parking. Walkable dining and to boardwalk. Quaint shopping."
United States
Kerry
$88 nightly
The price is $101
Dec 15 - Dec 16
Total with taxes and fees
The Niantic Inn
Exterior
The Shoals Suites and Slips

The Shoals Suites and Slips

The Shoals Suites and Slips
3.5 star property
2.5 mi from The Heights
9.4 out of 10, Exceptional, (228)
"Food!"
United States
Ryan
$175 nightly
The price is $201
Dec 17 - Dec 18
Total with taxes and fees
The Shoals Suites and Slips
Exterior
Shorewood Inn

Shorewood Inn

Shorewood Inn
2.5 star property
15.2 mi 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
$92 nightly
The price is $105
Dec 14 - Dec 15
Total with taxes and fees
Shorewood Inn
Property grounds
Clinton Motel

Clinton Motel

Clinton Motel
2.5 star property
15.8 mi from The Heights
8.6 out of 10, Excellent, (297)
"Great staff and clean rooms"
United States
Tyler
$78 nightly
The price is $90
Dec 14 - Dec 15
Total with taxes and fees
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
14.5 mi from The Heights
8.0 out of 10, Very Good, (1001)
"A welcoming place with some nice touches."
United States
Leslie
$79 nightly
The price is $91
Dec 21 - Dec 22
Total with taxes and fees
Pier Blue Inn Old Saybrook - Essex
Resort view
Sound View Greenport

Sound View Greenport

Sound View Greenport
4.0 star property
2.4 mi from The Heights
8.6 out of 10, Excellent, (598)
"Staff was amazing , room clean view phenomenal "
United States
Denise
$212 nightly
The price is $242
Jan 13 - Jan 14, 2026
Total with taxes and fees
Sound View Greenport
Individually decorated, individually furnished, desk, laptop workspace
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
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
Indoor pool, open 9:00 AM to 9:00 PM, sun loungers
Quality Inn Old Saybrook - Westbrook

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, (1002)
"Staff was kind. Easy, comfortable stay."
United States
Jake
$101 nightly
The price is $116
Dec 21 - Dec 22
Total with taxes and fees
Quality Inn Old Saybrook - Westbrook
Sport court
The Atlantic Hotel

The Atlantic Hotel

The Atlantic Hotel
2.5 star property
13.8 mi from The Heights
7.2 out of 10, Good, (974)
"Great hotel for a quick stay - very friendly staff"
United States
Dianne
$138 nightly
The price is $158
Dec 28 - Dec 29
Total with taxes and fees
The Atlantic Hotel
Exterior
Zey Hotel

Zey Hotel

Zey Hotel
3.5 star property
1.7 mi 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
$182 nightly
The price is $208
Dec 28 - Dec 29
Total with taxes and fees
Zey Hotel
Property entrance
The Sagaponack

The Sagaponack

The Sagaponack
3.0 star property
10.6 mi from The Heights
8.8 out of 10, Excellent, (212)
"Clean & amenities, staff friendly Thank you "
United States
Archil
$176 nightly
The price is $202
Dec 19 - Dec 20
Total with taxes and fees
The Sagaponack
Desk, free WiFi, bed sheets
Southampton Long Island Hotel

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 12 - Jan 13, 2026
Total with taxes and fees
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
16.2 mi from The Heights
9.4 out of 10, Exceptional, (312)
"Relaxing stay"
United States
Kristin
$201 nightly
The price is $229
Dec 28 - Dec 29
Total with taxes and fees
Aqua by American Beech - Adults Only
Terrace/patio
American Beech Hotel

American Beech Hotel

American Beech Hotel
3.5 star property
1.6 mi from The Heights
8.8 out of 10, Excellent, (195)
"The property was clean beautiful and pleasant. Loved the trendy decor."
United States
Jennifer
$234 nightly
The price is $267
Dec 14 - Dec 15
Total with taxes and fees
American Beech Hotel
Beach bar
Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
1.4 mi from The Heights
9.8 out of 10, Exceptional, (141)
"Great get away "
United States
Charles
$215 nightly
The price is $246
Jan 11 - Jan 12, 2026
Total with taxes and fees
Silver Sands Motel & Beach Bungalows
Bar (on property)
The Hampton Maid

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 29 - Dec 30
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

Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"Holiday family tradition!"
Donald 1-night trip
Posted 19 hours ago
Water's Edge Resort & Spa

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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