Hotels in The Heights, Shelter Island Heights

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Check prices for these dates

Tonight
21 Oct - 22 Oct
Tomorrow
22 Oct - 23 Oct
This weekend
24 Oct - 26 Oct
Next weekend
31 Oct - 2 Nov

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Top 10 Hotels in 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. "
United States
Neal
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 ! "
United States
Maureen
The price is RM781
RM892 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, (1015)
"Beautiful property, we loved our room, friendly staff. "
United States
Natalie
The price is RM1,015
RM1,273 total
includes taxes & fees
6 Nov - 7 Nov
Saybrook Point Resort & Marina
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, (65)
"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
Hampton Bays Hotel on Main
Property grounds
Pier Blue Inn Old Saybrook - Essex
Pier Blue Inn Old Saybrook - Essex
2.0 star property
7.8 out of 10, Good, (1018)
"Staff was incredibly communicative, kind, and patient. Definitely recommend and we would stay again!"
United States
Laura
The price is RM338
RM389 total
includes taxes & fees
22 Oct - 23 Oct
Pier Blue Inn Old Saybrook - Essex
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"
United States
angelica
The price is RM883
RM1,089 total
includes taxes & fees
26 Oct - 27 Oct
Water's Edge Resort & Spa
Exterior
Madison Beach Hotel
Madison Beach Hotel
4.0 star property
9.4 out of 10, Exceptional, (324)
"the staff was exceptional and our dinner was very good"
United States
john
The price is RM1,036
RM1,191 total
includes taxes & fees
30 Oct - 31 Oct
Madison Beach Hotel
View from room
The Harbor Front Inn
The Harbor Front Inn
3.5 star property
8.8 out of 10, Excellent, (524)
"Great location ,beautiful hotel,nice staff"
United States
ROBERT
The price is RM698
RM1,004 total
includes taxes & fees
2 Nov - 3 Nov
The Harbor Front Inn
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
7.8 out of 10, Good, (1013)
"Breakfast was bomb"
United States
Jostiena
The price is RM395
RM454 total
includes taxes & fees
2 Nov - 3 Nov
Quality Inn Old Saybrook - Westbrook
Outdoor pool
The Atlantic Hotel
The Atlantic Hotel
2.5 star property
7.2 out of 10, Good, (956)
"Love the area love the room size clean parking was perfect "
United States
Sherwood
The Atlantic 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."
United States
kayla c
Ocean Vista Resort
Exterior
Zey Hotel
Zey Hotel
3.5 star property
9.2 out of 10, Wonderful, (280)
"Clean and quiet right on a main street with plenty of shopping and dining. Very close to the vineyards. Great stay."
United States
Alexandra
The price is RM1,236
RM1,412 total
includes taxes & fees
26 Oct - 27 Oct
Zey Hotel
Property grounds
Liberty Inn
Liberty Inn
2.0 star property
7.4 out of 10, Good, (634)
"Quiet, clean, comfy. Bit dated but tucked away and close to private beach! "
United States
Kimberly A
The price is RM338
RM389 total
includes taxes & fees
2 Nov - 3 Nov
Liberty 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"
United States
Brian
The price is RM302
RM348 total
includes taxes & fees
2 Nov - 3 Nov
Econo Lodge Inn & Suites Old Saybrook Westbrook
Property grounds
The Hampton Maid
The Hampton Maid
2.5 star property
9.0 out of 10, Wonderful, (673)
"Love this place "
United States
Diane
The Hampton Maid
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, (431)
"A solid inexpensive stay in the Hamptons. Staff are very accommodating, they helped guide us when there was an upcoming storm. Room was comfortable and clean. "
United States
Michelle
The price is RM453
RM585 total
includes taxes & fees
2 Nov - 3 Nov
Hamlet Inn
Seasonal outdoor pool, pool umbrellas, pool loungers
Sound View Greenport
Sound View Greenport
4.0 star property
8.4 out of 10, Very good, (580)
"Loved everything about my stay at the Sound view !! "
United States
Sabrina
The price is RM943
RM1,285 total
includes taxes & fees
26 Oct - 27 Oct
Sound View Greenport
Private kitchen
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."
United States
Maggie
The price is RM532
RM608 total
includes taxes & fees
22 Oct - 23 Oct
Hampton's Vacation Inn
Outdoor pool
Sag Harbor Inn
Sag Harbor Inn
3.5 star property
9.4 out of 10, Exceptional, (559)
"Great place to stay!"
United States
Kim
The price is RM795
RM908 total
includes taxes & fees
2 Nov - 3 Nov
Sag Harbor Inn
Terrace/patio
Sea Crest Resort
Sea Crest Resort
2.5 star property
9.2 out of 10, Wonderful, (496)
"Perfect location!"
United States
Bernadette
The price is RM725
RM920 total
includes taxes & fees
5 Nov - 6 Nov
Sea Crest Resort
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 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

Madison Beach Hotel

Madison Beach Hotel

10/10 Excellent
"Great ocean view "
Julian M 1-night trip
Posted 3 days ago
Madison Beach 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.