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Find hotels in The Heights, Shelter Island Heights

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Dec 12 - Dec 14
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Our top choices for The Heights hotels

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
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 star property
14 mi from The Heights
9.6 out of 10, Exceptional, (1002)
"Excellent food, in addition to friendly and helpful staff."
United States
marybeth
$312 nightly
The price is $359
Dec 15 - Dec 16
Total with taxes and fees
Saybrook Point Resort & Marina
Exterior
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 star property
14.5 mi from The Heights
8.8 out of 10, Excellent, (1002)
"Yes! Ease of registration! The staff helped us with dinning suggestions, hotel programs and amenities!"
United States
Bruce
$244 nightly
The price is $281
Dec 10 - Dec 11
Total with taxes and fees
Water's Edge Resort & Spa
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, (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
Exterior
Madison Beach Hotel

Madison Beach Hotel

4.0 star property
18.5 mi from The Heights
9.4 out of 10, Exceptional, (339)
"The Spa was wonderful and the staff was attentive and helpful. "
United States
Emma
$242 nightly
The price is $278
Jan 1 - Jan 2, 2026
Total with taxes and fees
Madison Beach Hotel
Deluxe Double Room, 1 King Bed, City View | In-room safe, individually decorated, individually furnished, desk
Hampton Bays Hotel on Main

Hampton Bays Hotel on Main

2.0 star property
16.5 mi from The Heights
7.2 out of 10, Good, (69)
"Needed a last minute place to stay and this was PERFECT!! Reasonably priced and the owner is lovely. The rooms have everything you need and there’s a bar on the property where you can play pool and have an after-dinner drink. Highly recommend!"
United States
Olivia
$117 nightly
The price is $134
Dec 17 - Dec 18
Total with taxes and fees
Hampton Bays Hotel on Main
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, (544)
"Awesome stay!!! Great Location "
United States
Bryan
$153 nightly
The price is $175
Dec 22 - Dec 23
Total with taxes and fees
The Harbor Front 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
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 15 - Dec 16
Total with taxes and fees
Quality Inn Old Saybrook - Westbrook
Exterior
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 23 - Dec 24
Total with taxes and fees
Zey Hotel
Outdoor pool
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 23 - Dec 24
Total with taxes and fees
The Atlantic Hotel
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 10 - Dec 11
Total with taxes and fees
Hamlet Inn
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 23 - Dec 24
Total with taxes and fees
The Hampton Maid
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
Dec 16 - Dec 17
Total with taxes and fees
Econo Lodge Inn & Suites Old Saybrook Westbrook
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
$98 nightly
The price is $113
Dec 15 - Dec 16
Total with taxes and fees
The Niantic Inn
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, (598)
"Staff was amazing , room clean view phenomenal "
United States
Denise
$175 nightly
The price is $200
Dec 24 - Dec 25
Total with taxes and fees
Sound View Greenport
Outdoor pool
Sag Harbor Inn

Sag Harbor Inn

3.5 star property
6.2 mi from The Heights
9.4 out of 10, Exceptional, (572)
"Very clean, helpful staff and convenient location."
United States
Gordon
$215 nightly
The price is $246
Dec 10 - Dec 11
Total with taxes and fees
Sag Harbor Inn
Property entrance
The Menhaden

The Menhaden

3.5 star property
1.5 mi from The Heights
9.6 out of 10, Exceptional, (171)
"Wonderful stay in a quaint hotel..The small town was amazing and had such cozy welcoming atmosphere! "
United States
Cory
$309 nightly
The price is $347
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Menhaden
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, (391)
"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
Exterior
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
$160 nightly
The price is $182
Dec 10 - Dec 11
Total with taxes and fees
Aqua by American Beech - Adults Only
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
$184 nightly
The price is $211
Dec 15 - Dec 16
Total with taxes and fees
The Sagaponack
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 Harbor Front Inn

The Harbor Front Inn

10/10 Excellent
"Yes"
Ray 1-night trip
Posted 18 hours ago
The Harbor Front 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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