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Find hotels in The Heights, Shelter Island Heights

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Dec 29 - Dec 30
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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 ₩150,120
₩171,529 total
includes taxes & fees
Jan 6 - Jan 7, 2026
House on Chase Creek
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, (445)
"Great weekend stay! staff was super kind and property was beautiful! "
United States
Chyanne
The price is ₩125,857
₩162,677 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Hamlet Inn
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, (1002)
"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
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 ₩112,449
₩129,316 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Clinton Motel
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, (711)
"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
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, (204)
"Good location. Nice people!! "
United States
Theresa
The price is ₩143,806
₩171,486 total
includes taxes & fees
Jan 27 - Jan 28, 2026
Southampton Long Island Hotel
Seasonal outdoor pool, pool umbrellas, sun loungers
Sound View Greenport

Sound View Greenport

Sound View Greenport
4.0 star property
3.8 km from The Heights
8.4 out of 10, Very Good, (601)
"Great view but a gas station has a better breakfast. "
United States
Michael
The price is ₩229,512
₩301,437 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Sound View Greenport
One Bedroom Harbor View Terrace Suite | 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, (554)
"Room and staff were amazing. "
United States
Manuel
The price is ₩194,840
₩261,803 total
includes taxes & fees
Jan 28 - Jan 29, 2026
The Harbor Front Inn
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, (463)
"We came in for a family wedding in the area and this hotel was a great location. The mexican restaurant that was down the street is fantastic, great margaritas ! Would definitely use this location again if we were out this way. Thank you for a wonderful stay !"
United States
Robert
The price is ₩96,634
₩111,129 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Econo Lodge Inn & Suites Old Saybrook Westbrook
Garden Suite King | Premium bedding, down comforters, 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, (232)
"Great stay, will definitely go again"
United States
ANTONIO J
The price is ₩267,413
₩305,518 total
includes taxes & fees
Jan 1 - Jan 2, 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, (412)
"Adorable boutique hotel with charming unique touches. "
United States
Mary
The price is ₩181,649
₩208,976 total
includes taxes & fees
Jan 22 - Jan 23, 2026
The Bentley Hotel Southampton
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, (1001)
"The very friendly staff made this stay enjoyable from The beginning. The hotel was very clean and comfy. "
United States
Virginia
The price is ₩139,697
₩160,652 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Quality Inn Old Saybrook - Westbrook
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
The Sagaponack

The Sagaponack

The Sagaponack
3.0 star property
17.1 km from The Heights
8.8 out of 10, Excellent, (216)
"Clean & amenities, staff friendly Thank you "
United States
Archil
The price is ₩232,251
₩322,995 total
includes taxes & fees
Jan 1 - Jan 2, 2026
The Sagaponack
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
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 ₩115,477
₩132,799 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Liberty Inn
Aerial view
Southampton Inn

Southampton Inn

Southampton Inn
3.0 star property
22 km from The Heights
8.6 out of 10, Excellent, (553)
"Rooms were very clean and spacious, gorgeous property "
Canada
Luna
The price is ₩288,332
₩352,904 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Southampton Inn
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
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 Hampton Maid
IPod dock, MP3 dock
The Captain Stannard

The Captain Stannard

The Captain Stannard
3.0 star property
24 km from The Heights
9.8 out of 10, Exceptional, (259)
"The Inn and staff were warm and welcoming, the facility exceptionally clean. Breakfast exceeded my expectations for a continental breakfast! Would absolutely stay again! "
United States
Lisa
The Captain Stannard
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

The Bentley Hotel Southampton

The Bentley Hotel Southampton

10/10 Excellent
"They really take care of us! The location is great! "
Cassiano 4-night trip
Posted 2 days ago
The Bentley Hotel Southampton

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.