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Our top choices for The Heights hotels

House on Chase Creek

House on Chase Creek
2.5 star property
The Heights
9.4 out of 10, Exceptional, (81 reviews)
" 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 Rp1.751.883
Rp2.001.720 total
includes taxes & fees
19 Feb - 20 Feb
House on Chase Creek

Zey Hotel

Zey Hotel
3.5 star property
2.7 km from The Heights
9.2 out of 10, Wonderful, (298 reviews)
"Quiet yet situated right in the heart of Greenport."
United States
Andrew
The price is Rp5.450.976
Rp6.227.741 total
includes taxes & fees
18 Feb - 19 Feb
Zey Hotel

Clinton Motel

Clinton Motel
2.5 star property
25.4 km from The Heights
8.6 out of 10, Excellent, (302 reviews)
"The room was comfortable and clean. A good value for the money."
United States
Michael
The price is Rp1.312.272
Rp1.509.113 total
includes taxes & fees
18 Feb - 19 Feb
Clinton Motel

The Niantic Inn

The Niantic Inn
2.5 star property
30.1 km from The Heights
9.2 out of 10, Wonderful, (140 reviews)
"Quiet and warm and clean. Nice touch from Housekeeping too! "
United States
Jessica
The price is Rp1.877.558
Rp2.159.192 total
includes taxes & fees
18 Feb - 19 Feb
The Niantic Inn

Westbrook Inn B&B

Westbrook Inn B&B
3.0 star property
24 km from The Heights
9.8 out of 10, Exceptional, (179 reviews)
"Charming, beautiful inn; excellent food and service."
United States
Michael
The price is Rp3.463.220
Rp3.844.174 total
includes taxes & fees
25 Feb - 26 Feb
Westbrook Inn B&B

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
28 km from The Heights
8.8 out of 10, Excellent, (305 reviews)
"Quiet place, went off season, cooked all meals in the room, good home base to explore the area."
United States
Jerry
The price is Rp2.216.730
Rp2.989.961 total
includes taxes & fees
19 Feb - 20 Feb
Windward Shores Ocean Resort

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, (1,002 reviews)
"Room was clean and warm and the staff was very friendly "
United States
Pattie
Pier Blue Inn Old Saybrook - Essex

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, (1,007 reviews)
"Hotel was very clean, staff was wonderful and the pool was so relaxing. It was a quick visit but definitely would stay again if I was in that area. "
United States
Kathleen
The price is Rp1.630.246
Rp1.874.783 total
includes taxes & fees
24 Feb - 25 Feb
Quality Inn Old Saybrook - Westbrook

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, (241 reviews)
"Great stay, will definitely go again"
United States
ANTONIO J
The price is Rp2.725.337
Rp3.113.696 total
includes taxes & fees
20 Feb - 21 Feb
The Shoals Suites and Slips

The 1770 House Restaurant & Inn

The 1770 House Restaurant & Inn
4.0 star property
19.4 km from The Heights
9.8 out of 10, Exceptional, (162 reviews)
"The staff was incredibly genuine and the property felt intimate and comfortable."
United States
Aniya
The price is Rp4.069.726
Rp5.563.697 total
includes taxes & fees
18 Feb - 19 Feb
The 1770 House Restaurant & Inn

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, (1,004 reviews)
"Great place!"
United States
Laura
The price is Rp3.290.198
Rp4.074.149 total
includes taxes & fees
25 Feb - 26 Feb
Water's Edge Resort & Spa

The Captain Stannard

The Captain Stannard
3.0 star property
24 km from The Heights
9.8 out of 10, Exceptional, (260 reviews)
"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

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, (70 reviews)
"Loved the 2 bar options on the property."
United States
Jennifer
The price is Rp2.378.240
Rp2.717.139 total
includes taxes & fees
20 Feb - 21 Feb
Hampton Bays Hotel on Main

The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
22.6 km from The Heights
9.6 out of 10, Exceptional, (436 reviews)
"Adorable room"
United States
Martin
The price is Rp2.123.461
Rp2.442.890 total
includes taxes & fees
23 Feb - 24 Feb
The Bentley Hotel Southampton

The Hampton Maid

The Hampton Maid
2.5 star property
24.7 km from The Heights
9.0 out of 10, Wonderful, (688 reviews)
"Great place to stay"
United States
Mitchell
The Hampton Maid

The Harbor Front Inn

The Harbor Front Inn
3.5 star property
2.4 km from The Heights
8.8 out of 10, Excellent, (567 reviews)
"Lovely hotel with great location in town. Great free breakfast and wonderful staff. We will return! "
United States
Pamela
The price is Rp2.146.742
Rp2.933.146 total
includes taxes & fees
3 Mar - 4 Mar
The Harbor Front Inn

Wainscott Woods Retreat

Wainscott Woods Retreat
2.5 star property
17.2 km from The Heights
7.0 out of 10, Good, (9 reviews)
"Newly Renovated and extremely clean, well kept, and inviting rooms. Staff could not be nicer and more accommodating. Location is ideally situated close to lots of shops, Goldbergs for bagels, East Hampton Beaches etc. Highly recommend this accommodation to anyone staying in the area."
United States
Ivan
The price is Rp4.802.411
Rp5.486.754 total
includes taxes & fees
18 Feb - 19 Feb
Wainscott Woods Retreat

Harpoon House

Harpoon House
3.0 star property
21.6 km from The Heights
8.4 out of 10, Very good, (149 reviews)
"Great spot!"
United States
Keith
Harpoon House

Vine & Sand

Vine & Sand
3.0 star property
7.9 km from The Heights
9.6 out of 10, Exceptional, (15 reviews)
"Wonderful stay"
United States
Judy
Vine & Sand

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, (144 reviews)
"Everything was excellent, best hotel on the north fork. "
United States
Dan
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.

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 Harbor Brewing Company, some noteworthy sights in the nearby area.

Top The Heights Hotel Reviews

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 12 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.