Search Hotels in The Heights, Shelter Island Heights

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
16 Oct - 17 Oct
Tomorrow
17 Oct - 18 Oct
This weekend
17 Oct - 19 Oct
Next weekend
24 Oct - 26 Oct

Filter by

Guest rating
Guest rating
Star rating

Top Trending Hotels Near The Heights, Shelter Island Heights

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. "
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 ! "
The price is ฿6,012
฿6,868 total
includes taxes & fees
3 Nov - 4 Nov
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. "
The price is ฿7,810
฿9,794 total
includes taxes & fees
6 Nov - 7 Nov
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!"
The price is ฿2,605
฿2,996 total
includes taxes & fees
19 Oct - 20 Oct
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!"
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"
The price is ฿6,797
฿8,377 total
includes taxes & fees
19 Oct - 20 Oct
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 "
The Atlantic Hotel
Indoor pool, open 9:00 AM to 9:00 PM, pool 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."
The price is ฿3,041
฿3,497 total
includes taxes & fees
2 Nov - 3 Nov
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"
The price is ฿7,973
฿9,169 total
includes taxes & fees
30 Oct - 31 Oct
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"
The price is ฿5,371
฿7,728 total
includes taxes & fees
2 Nov - 3 Nov
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."
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."
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 "
The price is ฿9,219
฿10,533 total
includes taxes & fees
17 Oct - 18 Oct
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. "
The price is ฿2,605
฿2,996 total
includes taxes & fees
2 Nov - 3 Nov
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 "
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."
The price is ฿4,098
฿4,681 total
includes taxes & fees
19 Oct - 20 Oct
Hampton's Vacation Inn
Seasonal outdoor pool, open 9:00 AM to 8:00 PM, free pool 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! "
The price is ฿5,312
฿6,069 total
includes taxes & fees
19 Oct - 20 Oct
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"
The price is ฿3,483
฿4,502 total
includes taxes & fees
2 Nov - 3 Nov
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"
The price is ฿2,326
฿2,675 total
includes taxes & fees
2 Nov - 3 Nov
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!"
The price is ฿6,117
฿6,989 total
includes taxes & fees
2 Nov - 3 Nov
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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

Baron's Cove

Baron's Cove

10/10 Excellent
"Parking was free and really easy. Great proximity to the main street of town—you can easily walk, but it's not too close where it gets loud at night. The front staff and cleaning team were all lovely and super helpful. We loved the coffee bar in the mornings. "
Katherine 3-night trip
Posted 2 weeks ago
Baron's Cove
The Atlantic Hotel

The Atlantic Hotel

10/10 Excellent
"Loved it"
Pelinsu 2-night trip
Posted 1 month ago
The Atlantic 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, The Chequit is the highest ranked property in The Heights. This hotel offers a restaurant and free parking. Another top choice in the area is House on Chase Creek.
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.