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.

Exterior
The Chequit
The Chequit
3.0 star property
9.0 out of 10, Wonderful, (37)
"A cozy room with great pillows and quiet. Perfect little place. "
$273 nightly
The price is $312
Nov 5 - Nov 6
Total with taxes and fees
The Chequit
View from property
House on Chase Creek
House on Chase Creek
2.5 star property
9.4 out of 10, Exceptional, (77)
" 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 ! "
$185 nightly
The price is $211
Nov 3 - Nov 4
Total with taxes and fees
House on Chase Creek
Exterior
Saybrook Point Resort & Marina
Saybrook Point Resort & Marina
3.5 star property
9.4 out of 10, Exceptional, (1012)
"Beautiful property, we loved our room, friendly staff. "
$291 nightly
The price is $334
Nov 6 - Nov 7
Total with taxes and fees
Saybrook Point Resort & Marina
Property grounds
Pier Blue Inn Old Saybrook - Essex
Pier Blue Inn Old Saybrook - Essex
2.0 star property
7.8 out of 10, Good, (1014)
"Staff was incredibly communicative, kind, and patient. Definitely recommend and we would stay again!"
$85 nightly
The price is $98
Oct 20 - Oct 21
Total with taxes and fees
Pier Blue Inn Old Saybrook - Essex
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
7.0 out of 10, Good, (64)
"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!"
$121 nightly
The price is $138
Nov 2 - Nov 3
Total with taxes and fees
Hampton Bays Hotel on Main
Exterior
Water's Edge Resort & Spa
Water's Edge Resort & Spa
3.5 star property
8.8 out of 10, Excellent, (1008)
"We love the stay everything was perfect"
$209 nightly
The price is $241
Oct 26 - Oct 27
Total with taxes and fees
Water's Edge Resort & Spa
Outdoor pool
The Atlantic Hotel
The Atlantic Hotel
2.5 star property
7.2 out of 10, Good, (955)
"Love the area love the room size clean parking was perfect "
$138 nightly
The price is $158
Nov 2 - Nov 3
Total with taxes and fees
The Atlantic Hotel
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
7.6 out of 10, Good, (1009)
"We have stayed there before so have been pleased with it."
$94 nightly
The price is $108
Nov 2 - Nov 3
Total with taxes and fees
Quality Inn Old Saybrook - Westbrook
Exterior
Madison Beach Hotel
Madison Beach Hotel
4.0 star property
9.4 out of 10, Exceptional, (323)
"the staff was exceptional and our dinner was very good"
$245 nightly
The price is $282
Oct 30 - Oct 31
Total with taxes and fees
Madison Beach Hotel
One Bedroom Harbor View Terrace Suite | View from room
The Harbor Front Inn
The Harbor Front Inn
3.5 star property
8.8 out of 10, Excellent, (523)
"Great location ,beautiful hotel,nice staff"
$197 nightly
The price is $225
Nov 2 - Nov 3
Total with taxes and fees
The Harbor Front Inn
Exterior
Zey Hotel
Zey Hotel
3.5 star property
9.2 out of 10, Wonderful, (279)
"Clean and quiet right on a main street with plenty of shopping and dining. Very close to the vineyards. Great stay."
$293 nightly
The price is $334
Oct 19 - Oct 20
Total with taxes and fees
Zey Hotel
View from property
Ocean Vista Resort
Ocean Vista Resort
2.5 star property
9.0 out of 10, Wonderful, (196)
"Such a beautiful place to stay. Pam at the front was so nice and welcoming. The room was clean it was quiet and everyone was friendly. Love that it has a private beach! Would 10/10 recommend it and deff will be going back."
$149 nightly
The price is $170
Oct 26 - Oct 27
Total with taxes and fees
Ocean Vista Resort
Property grounds
The Hampton Maid
The Hampton Maid
2.5 star property
9.0 out of 10, Wonderful, (671)
"Love this place "
$188 nightly
The price is $215
Nov 3 - Nov 4
Total with taxes and fees
The Hampton Maid
Property grounds
Liberty Inn
Liberty Inn
2.0 star property
7.4 out of 10, Good, (632)
"Well located for getting to the places we wanted to be. This is an older property, but well taken care of and service was very good. I wouldn’t hesitate to stay here again. "
$77 nightly
The price is $89
Nov 16 - Nov 17
Total with taxes and fees
Liberty Inn
Property grounds
Greenporter Hotel
Greenporter Hotel
2.0 star property
9.2 out of 10, Wonderful, (269)
"Staff was amazing and this hotel is in the perfect location "
$119 nightly
The price is $137
Oct 19 - Oct 20
Total with taxes and fees
Greenporter Hotel
Apartment, 2 Bedrooms | Private kitchen | Microwave, coffee/tea maker, cookware/dishes/utensils
Hampton's Vacation Inn
Hampton's Vacation Inn
2.5 star property
9.0 out of 10, Wonderful, (318)
"A great Hampton location that's less than a thirty minutes drive from Coopers Beach and South Hampton main street."
$140 nightly
The price is $160
Oct 19 - Oct 20
Total with taxes and fees
Hampton's Vacation Inn
Seasonal outdoor pool, open 9:00 AM to 8:00 PM, free cabanas
Bayview Resort
Bayview Resort
2.5 star property
8.8 out of 10, Excellent, (452)
"Staff was fantastic, room was always clean and the area was perfect! "
$163 nightly
The price is $187
Oct 19 - Oct 20
Total with taxes and fees
Bayview Resort
Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas
Hamlet Inn
Hamlet Inn
2.0 star property
8.6 out of 10, Excellent, (430)
"Great Staff"
$137 nightly
The price is $154
Nov 2 - Nov 3
Total with taxes and fees
Hamlet Inn
Exterior
Econo Lodge Inn & Suites Old Saybrook Westbrook
Econo Lodge Inn & Suites Old Saybrook Westbrook
2.0 star property
7.2 out of 10, Good, (456)
"the so-called breakfast was absolute minimum only thing available was make your own waffle"
$72 nightly
The price is $82
Nov 2 - Nov 3
Total with taxes and fees
Econo Lodge Inn & Suites Old Saybrook Westbrook
Outdoor pool
Sag Harbor Inn
Sag Harbor Inn
3.5 star property
9.4 out of 10, Exceptional, (557)
"Great place to stay!"
$209 nightly
The price is $239
Nov 2 - Nov 3
Total with taxes and fees
Sag Harbor Inn
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
"We love the stay everything was perfect"
angelica 1-night trip
Posted 2 days 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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