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Search Hotels in The Heights, Shelter Island Heights

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18 Dec - 19 Dec
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19 Dec - 20 Dec
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19 Dec - 21 Dec
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26 Dec - 28 Dec

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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 2.741.847 ₫
3.132.862 ₫ total
includes taxes & fees
12 Jan - 13 Jan 2026
House on Chase Creek
Exterior
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, (228)
"Room was clean and comfortable. Easy check in and check out. Staff very accommodating. "
United States
James
The price is 4.884.137 ₫
5.580.128 ₫ total
includes taxes & fees
30 Dec - 31 Dec
The Shoals Suites and Slips
Lobby lounge
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, (547)
"Awesome stay!!! Great Location "
United States
Bryan
The price is 3.532.060 ₫
5.324.410 ₫ total
includes taxes & fees
22 Dec - 23 Dec
The Harbor Front Inn
Golf
Hamlet Inn

Hamlet Inn

Hamlet Inn
2.0 star property
23.1 km from The Heights
8.6 out of 10, Excellent, (443)
"Great weekend stay! staff was super kind and property was beautiful! "
United States
Chyanne
The price is 2.701.561 ₫
3.491.491 ₫ total
includes taxes & fees
23 Dec - 24 Dec
Hamlet Inn
Reception
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, (398)
"great cost-effective option; room was very spacious and clean."
United States
Isadora
The price is 3.294.681 ₫
3.790.503 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
The Bentley Hotel Southampton
Resort view
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, (598)
"Staff was amazing , room clean view phenomenal "
United States
Denise
The price is 4.191.895 ₫
6.078.248 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
Sound View Greenport
Property grounds
Clinton Motel

Clinton Motel

Clinton Motel
2.5 star property
25.4 km from The Heights
8.6 out of 10, Excellent, (297)
"Great staff and clean rooms"
United States
Tyler
The price is 2.053.818 ₫
2.361.891 ₫ total
includes taxes & fees
19 Dec - 20 Dec
Clinton Motel
Exterior
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
Property entrance
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 4.006.162 ₫
5.630.271 ₫ total
includes taxes & fees
22 Dec - 23 Dec
The Sagaponack
Terrace/patio
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 4.713.249 ₫
6.438.193 ₫ total
includes taxes & fees
23 Dec - 24 Dec
American Beech Hotel
Exterior
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina
3.5 star property
22.6 km from The Heights
9.6 out of 10, Exceptional, (1002)
"Wonderful stay in a beautiful setting."
United States
Deborah
The price is 8.136.279 ₫
10.014.996 ₫ total
includes taxes & fees
29 Dec - 30 Dec
Saybrook Point Resort & Marina
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, (1000)
"A welcoming place with some nice touches."
United States
Leslie
Pier Blue Inn Old Saybrook - Essex
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, (1004)
"The staff was friendly. The room was good. "
United States
Narida
The price is 2.663.381 ₫
3.062.888 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
Quality Inn Old Saybrook - Westbrook
Building design
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 5.661.165 ₫
6.467.881 ₫ total
includes taxes & fees
23 Dec - 24 Dec
Sag Harbor Inn
Sports court
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
Breakfast, lunch, brunch served; local cuisine
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 5.266.200 ₫
6.445.566 ₫ total
includes taxes & fees
19 Dec - 20 Dec
Southampton Inn
Property grounds
Liberty Inn

Liberty Inn

Liberty Inn
2.0 star property
25.8 km from The Heights
7.4 out of 10, Good, (640)
"Great little place to stay with friendly staff and clean room"
United States
Carolan
The price is 2.109.113 ₫
2.425.480 ₫ total
includes taxes & fees
29 Dec - 30 Dec
Liberty Inn
View from property
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
Individually decorated, individually furnished, desk, laptop workspace
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, (460)
"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 1.764.967 ₫
2.029.712 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Econo Lodge Inn & Suites Old Saybrook Westbrook
Beach bar
Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
2.3 km from The Heights
9.8 out of 10, Exceptional, (142)
"Great get away "
United States
Charles
Silver Sands Motel & Beach Bungalows
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

Hampton Bays Hotel on Main

Hampton Bays Hotel on Main

10/10 Excellent
"Loved the 2 bar options on the property."
Jennifer 1-night trip
Posted 2 months ago
Hampton Bays Hotel on Main

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.
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.