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Hotels in The Heights, Shelter Island Heights

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Tonight
22 Dec - 23 Dec
Tomorrow
23 Dec - 24 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

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Our top choices for The Heights hotels

View from property
House on Chase Creek

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 RM424
RM485 total
includes taxes & fees
6 Jan - 7 Jan 2026
House on Chase Creek
Seasonal outdoor pool, pool umbrellas, pool loungers
Sound View Greenport

Sound View Greenport

Sound View Greenport
4.0 star property
3.8 km from The Heights
8.6 out of 10, Excellent, (599)
"Staff was amazing , room clean view phenomenal "
United States
Denise
The price is RM649
RM941 total
includes taxes & fees
23 Dec - 24 Dec
Sound View Greenport
View from room
The Harbor Front Inn

The Harbor Front Inn

The Harbor Front Inn
3.5 star property
2.4 km from The Heights
8.8 out of 10, Excellent, (548)
"Awesome stay!!! Great Location "
United States
Bryan
The price is RM547
RM824 total
includes taxes & fees
23 Dec - 24 Dec
The Harbor Front Inn
Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas
Hamlet Inn

Hamlet Inn

Hamlet Inn
2.0 star property
23.1 km from The Heights
8.6 out of 10, Excellent, (444)
"Great weekend stay! staff was super kind and property was beautiful! "
United States
Chyanne
The price is RM404
RM522 total
includes taxes & fees
23 Dec - 24 Dec
Hamlet Inn
Premium bedding, down duvets, individually decorated
The Shoals Suites and Slips

The Shoals Suites and Slips

The Shoals Suites and Slips
3.5 star property
4 km from The Heights
9.4 out of 10, Exceptional, (230)
"Great stay, will definitely go again"
United States
ANTONIO J
The price is RM756
RM864 total
includes taxes & fees
1 Jan - 2 Jan 2026
The Shoals Suites and Slips
Terrace/patio
The Bentley Hotel Southampton

The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
22.6 km from The Heights
9.6 out of 10, Exceptional, (401)
"great cost-effective option; room was very spacious and clean."
United States
Isadora
The price is RM510
RM587 total
includes taxes & fees
4 Jan - 5 Jan 2026
The Bentley Hotel Southampton
Property grounds
Pier Blue Inn Old Saybrook - Essex

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, (1007)
"Staff was courteous, and bed was comfortable. The room hasn't had decor updated for decades. Fine for an overnight if you are just traveling through area for the price. "
United States
sue
Pier Blue Inn Old Saybrook - Essex
Exterior
American Beech Hotel

American Beech Hotel

American Beech Hotel
3.5 star property
2.6 km from The Heights
8.8 out of 10, Excellent, (195)
"The property was clean beautiful and pleasant. Loved the trendy decor."
United States
Jennifer
The price is RM730
RM997 total
includes taxes & fees
23 Dec - 24 Dec
American Beech Hotel
Terrace/patio
Shorewood Inn

Shorewood Inn

Shorewood Inn
2.5 star property
24.5 km from The Heights
8.4 out of 10, Very good, (710)
"Couldn't have been easier! The woman at the front desk was warm and welcoming, the room was super clean and cute with the heat turned on full blast in anticipation of my arrival. Adorable backyard with seating, too. Super hot water in the shower. Perfect for an impromptu winter getaway. "
United States
Mahlon
Shorewood Inn
Indoor pool, open 9:00 AM to 9:00 PM, pool loungers
Quality Inn Old Saybrook - Westbrook

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, (1002)
"The very friendly staff made this stay enjoyable from The beginning. The hotel was very clean and comfy. "
United States
Virginia
The price is RM412
RM474 total
includes taxes & fees
29 Dec - 30 Dec
Quality Inn Old Saybrook - Westbrook
Exterior
The Sagaponack

The Sagaponack

The Sagaponack
3.0 star property
17.1 km from The Heights
8.8 out of 10, Excellent, (215)
"Clean & amenities, staff friendly Thank you "
United States
Archil
The price is RM657
RM913 total
includes taxes & fees
29 Dec - 30 Dec
The Sagaponack
Aerial view
Southampton Inn

Southampton Inn

Southampton Inn
3.0 star property
22 km from The Heights
8.6 out of 10, Excellent, (549)
"Such a great location!"
United States
Elizabeth
The price is RM815
RM998 total
includes taxes & fees
23 Dec - 24 Dec
Southampton Inn
Exterior
Aqua by American Beech - Adults Only

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
Journey East Hampton

Journey East Hampton

Journey East Hampton
4.0 star property
20.7 km from The Heights
9.0 out of 10, Wonderful, (160)
"We were able to access many beaches with the beach pass that came with the stay. That was the main reason we wanted to stay there. The rooms were very nice, spacious and comfortable. "
United States
Sarah
Journey East Hampton
Outdoor pool
Sag Harbor Inn

Sag Harbor Inn

Sag Harbor Inn
3.5 star property
10 km from The Heights
9.4 out of 10, Exceptional, (576)
"Very clean, helpful staff and convenient location."
United States
Gordon
The price is RM876
RM1,001 total
includes taxes & fees
23 Dec - 24 Dec
Sag Harbor Inn
Outdoor pool
The Atlantic Hotel

The Atlantic Hotel

The Atlantic Hotel
2.5 star property
22.1 km from The Heights
7.2 out of 10, Good, (975)
"Great hotel for a quick stay - very friendly staff"
United States
Dianne
The Atlantic Hotel
Desk, free WiFi, bed sheets
Southampton Long Island Hotel

Southampton Long Island Hotel

Southampton Long Island Hotel
2.5 star property
20.9 km from The Heights
8.6 out of 10, Excellent, (203)
"Good location. Nice people!! "
United States
Theresa
The price is RM484
RM577 total
includes taxes & fees
20 Jan - 21 Jan 2026
Southampton Long Island Hotel
Property grounds
Clinton Motel

Clinton Motel

Clinton Motel
2.5 star property
25.4 km from The Heights
8.6 out of 10, Excellent, (298)
"Great staff and clean rooms"
United States
Tyler
The price is RM318
RM366 total
includes taxes & fees
28 Dec - 29 Dec
Clinton Motel
Property grounds
The Hampton Maid

The Hampton Maid

The Hampton Maid
2.5 star property
24.7 km from The Heights
9.0 out of 10, Wonderful, (688)
"Great place to stay"
United States
Mitchell
The price is RM1,156
RM1,320 total
includes taxes & fees
26 Dec - 27 Dec
The Hampton Maid
Exterior
Econo Lodge Inn & Suites Old Saybrook Westbrook

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, (462)
"A very clean and convenient hotel. It’s close to the beach and provides a parking pass for local beach with a refundable deposit."
United States
Anonymous traveller
The price is RM273
RM314 total
includes taxes & fees
4 Jan - 5 Jan 2026
Econo Lodge Inn & Suites Old Saybrook Westbrook
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

Sag Harbor Inn

Sag Harbor Inn

10/10 Excellent
"love this Inn, it is very welcoming, a bit old school, which we love! Room is large , parking free and easy, and we love the breakfast room and all day coffee."
Joanne 3-night trip
Posted 6 days ago
Sag Harbor Inn

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, House on Chase Creek is the highest ranked property in The Heights. This guest house offers free parking and free WiFi.
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.

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