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Find hotels in The Heights, Shelter Island Heights from ￥12,039

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Dec 1 - Dec 2
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Dec 2 - Dec 3
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Discover 3,985 The Heights hotels and places to stay, with room rates, reviews, and availability. Most hotels are fully refundable.

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
The price is ￥28,871
￥32,985 total
includes taxes & fees
Dec 2 - Dec 3
House on Chase Creek
Exterior
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 star property
22.6 km from The Heights
9.4 out of 10, Exceptional, (1014)
"Lovely rooms and loved the fireplace. Great stay. Awesome few days away from real life!"
United States
Andrew
The price is ￥42,951
￥53,299 total
includes taxes & fees
Dec 17 - Dec 18
Saybrook Point Resort & Marina
Exterior
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 star property
23.3 km from The Heights
8.8 out of 10, Excellent, (1008)
"We love the stay everything was perfect"
United States
angelica
The price is ￥24,785
￥31,198 total
includes taxes & fees
Dec 3 - Dec 4
Water's Edge Resort & Spa
Property grounds
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2.0 star property
23.3 km from The Heights
8.0 out of 10, Very Good, (1006)
"A welcoming place with some nice touches."
United States
Leslie
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
26.5 km 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
Hampton Bays Hotel on Main
Exterior
Madison Beach Hotel

Madison Beach Hotel

4.0 star property
29.8 km from The Heights
9.4 out of 10, Exceptional, (338)
"Staff and hotel are lovely "
United States
Steven
The price is ￥38,292
￥44,036 total
includes taxes & fees
Dec 7 - Dec 8
Madison Beach 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
26.5 km from The Heights
7.8 out of 10, Good, (1015)
"Staff was kind. Easy, comfortable stay."
United States
Jake
The price is ￥15,798
￥18,167 total
includes taxes & fees
Dec 8 - Dec 9
Quality Inn Old Saybrook - Westbrook
One Bedroom Harbor View Terrace Suite | View from room
The Harbor Front Inn

The Harbor Front Inn

3.5 star property
2.4 km from The Heights
8.8 out of 10, Excellent, (539)
"Amazing property, rooms, and staff. Book a room with a balcony for amazing views!"
United States
Matthew
The price is ￥16,290
￥26,255 total
includes taxes & fees
Dec 29 - Dec 30
The Harbor Front Inn
Outdoor pool
The Atlantic Hotel

The Atlantic Hotel

2.5 star property
22.1 km from The Heights
7.2 out of 10, Good, (973)
"Great hotel for a quick stay - very friendly staff"
United States
Dianne
The Atlantic Hotel
Exterior
Zey Hotel

Zey Hotel

3.5 star property
2.7 km 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
Zey Hotel
Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas
Hamlet Inn

Hamlet Inn

2.0 star property
23.1 km from The Heights
8.6 out of 10, Excellent, (439)
"Great weekend stay! staff was super kind and property was beautiful! "
United States
Chyanne
The price is ￥16,024
￥20,709 total
includes taxes & fees
Dec 2 - Dec 3
Hamlet Inn
Property grounds
The Hampton Maid

The Hampton Maid

2.5 star property
24.7 km from The Heights
9.0 out of 10, Wonderful, (687)
"Great place to stay"
United States
Mitchell
The Hampton Maid
Exterior
Econo Lodge Inn & Suites Old Saybrook Westbrook

Econo Lodge Inn & Suites Old Saybrook Westbrook

2.0 star property
23.3 km from The Heights
7.2 out of 10, Good, (460)
"🙂"
United States
Jared
The price is ￥10,469
￥12,039 total
includes taxes & fees
Dec 8 - Dec 9
Econo Lodge Inn & Suites Old Saybrook Westbrook
Outdoor pool
Sag Harbor Inn

Sag Harbor Inn

3.5 star property
10 km from The Heights
9.4 out of 10, Exceptional, (569)
"We had lovely stay, the staff was knowledgeable, efficient, and friendly. Will visit again! "
United States
Lori
The price is ￥30,221
￥34,527 total
includes taxes & fees
Dec 2 - Dec 3
Sag Harbor Inn
Seasonal outdoor pool, pool umbrellas, sun loungers
Sound View Greenport

Sound View Greenport

4.0 star property
3.8 km from The Heights
8.6 out of 10, Excellent, (596)
"Staff was amazing , room clean view phenomenal "
United States
Denise
The price is ￥25,035
￥36,246 total
includes taxes & fees
Dec 2 - Dec 3
Sound View Greenport
Standard Studio, 1 King Bed, Non Smoking | Premium bedding, free WiFi, bed sheets
The Niantic Inn

The Niantic Inn

2.5 star property
30.1 km from The Heights
9.0 out of 10, Wonderful, (123)
"Great location. Nice and clean room and property"
United States
Eric
The price is ￥13,775
￥15,841 total
includes taxes & fees
Dec 8 - Dec 9
The Niantic Inn
Terrace/patio
The Bentley Hotel Southampton

The Bentley Hotel Southampton

2.0 star property
22.6 km from The Heights
9.6 out of 10, Exceptional, (388)
"great cost-effective option; room was very spacious and clean."
United States
Isadora
The price is ￥18,356
￥21,129 total
includes taxes & fees
Dec 11 - Dec 12
The Bentley Hotel Southampton
Exterior
Aqua by American Beech - Adults Only

Aqua by American Beech - Adults Only

2.5 star property
26 km from The Heights
9.4 out of 10, Exceptional, (312)
"Relaxing stay"
United States
Kristin
Aqua by American Beech - Adults Only
Exterior
The Sagaponack

The Sagaponack

3.0 star property
17.1 km from The Heights
8.8 out of 10, Excellent, (209)
"An absolute gem of a place to stay. The rooms are full of character and charm, it’s The Hamptons all the way. Great location, too. "
United States
Brad
The price is ￥22,985
￥32,505 total
includes taxes & fees
Dec 7 - Dec 8
The Sagaponack
Property entrance
The Menhaden

The Menhaden

3.5 star property
2.4 km from The Heights
9.6 out of 10, Exceptional, (170)
"Hotel manager was great! Loved the firepits outside "
United States
Lisa
The price is ￥28,315
￥38,596 total
includes taxes & fees
Jan 1 - Jan 2, 2026
The Menhaden
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
"Staff"
Victor 1-night trip
Posted 2 days ago
Water's Edge Resort & Spa

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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 neighborhood has to offer. Be sure to check out 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, House on Chase Creek is the highest ranked property in The Heights. This guesthouse offers free parking and free WiFi.
How many hotels will I 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 accommodations in The Heights.
If I need to cancel my hotel reservation in The Heights, will I receive a refund?
Yes, most hotel bookings are fully refundable if cancelled prior to the hotel's cancellation deadline, which is usually within 24-48 hours of your scheduled arrival. If you have a reservation that's non-refundable, you may still be able to cancel and get a refund within 24 hours of your booking. Plug in your dates, click on "Search", then use the "fully refundable" filter to get the best options available in The Heights.
Where can I learn more about changing or cancelling my trip to The Heights?
To find more details about picking new dates or cancelling your trip to The Heights, click here.
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.