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Find hotels in The Heights, Shelter Island Heights from NT$2,405

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Dec 15 - Dec 16
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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 NT$3,248
NT$3,711 total
includes taxes & fees
Jan 6 - 2026/1/7
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)
"Food!"
United States
Ryan
The price is NT$5,786
NT$6,611 total
includes taxes & fees
Dec 16 - Dec 17
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 NT$4,183
NT$6,306 total
includes taxes & fees
Dec 16 - Dec 17
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, (442)
"Great weekend stay! staff was super kind and property was beautiful! "
United States
Chyanne
The price is NT$2,779
NT$3,592 total
includes taxes & fees
Dec 16 - Dec 17
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, (396)
"great cost-effective option; room was very spacious and clean."
United States
Isadora
The price is NT$3,903
NT$4,491 total
includes taxes & fees
Dec 21 - Dec 22
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 NT$4,966
NT$7,201 total
includes taxes & fees
Dec 16 - Dec 17
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 NT$2,433
NT$2,798 total
includes taxes & fees
Dec 16 - Dec 17
Clinton Motel
Exterior
Shorewood Inn

Shorewood Inn

Shorewood Inn
2.5 star property
24.5 km from The Heights
8.6 out of 10, Excellent, (709)
"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, (214)
"Clean & amenities, staff friendly Thank you "
United States
Archil
The price is NT$4,745
NT$6,668 total
includes taxes & fees
Dec 22 - Dec 23
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 NT$5,584
NT$7,627 total
includes taxes & fees
Dec 16 - Dec 17
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 NT$9,639
NT$11,865 total
includes taxes & fees
Dec 21 - Dec 22
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, (1003)
"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, sun 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 NT$3,155
NT$3,629 total
includes taxes & fees
Dec 22 - Dec 23
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, (575)
"Very clean, helpful staff and convenient location."
United States
Gordon
The price is NT$6,707
NT$7,662 total
includes taxes & fees
Dec 16 - Dec 17
Sag Harbor Inn
Sport 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, (974)
"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, (548)
"Such a great location!"
United States
Elizabeth
The price is NT$6,239
NT$7,636 total
includes taxes & fees
Dec 16 - Dec 17
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 NT$2,499
NT$2,873 total
includes taxes & fees
Dec 16 - Dec 17
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)
"🙂"
United States
Jared
The price is NT$2,091
NT$2,405 total
includes taxes & fees
Jan 4 - 2026/1/5
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 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
"Holiday family tradition!"
Donald 1-night trip
Posted 3 days ago
Water's Edge Resort & Spa

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 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.