Photo by Erisa Dilo

The Heights Hotels, Shelter Island Heights

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
23 July - 24 July
Tomorrow
24 July - 25 July
This weekend
25 July - 27 July
Next weekend
1 Aug - 3 Aug

Filter by

Guest rating
Guest rating
Property class

4043 Cheap Hotels in The Heights - Specials, Reviews, & Last Minute Deals

Shorewood Inn
Relax in a serene outdoor space surrounded by lush greenery, perfect for dining and socializing.

Shorewood Inn

2.5 star property
8.6 out of 10, Excellent, (659)
"Good place to stay"
Shorewood Inn
Greenporter Hotel
Relax by the fire pit surrounded by comfortable seating and a serene pool view.

Greenporter Hotel

2.0 star property
9.2 out of 10, Wonderful, (142)
"Great place "
Greenporter Hotel
Saybrook Point Resort & Marina
Enjoy a tranquil waterfront setting with a fire pit table and stunning views of the marina.

Saybrook Point Resort & Marina

3.5 star property
9.4 out of 10, Exceptional, (1008)
"Beautiful spot and great accommodations—can’t wait to return! "
The price is AU$647
includes taxes & fees
12 Aug - 13 Aug
Saybrook Point Resort & Marina
The Chequit
Relax and dine al fresco in this serene outdoor seating area, surrounded by lush trees and a golf course view.

The Chequit

3.0 star property
8.8 out of 10, Excellent, (31)
"we loved it!"
The Chequit
Pier Blue Inn Old Saybrook - Essex
Welcome to Pier Blue Guesthouse, surrounded by lush greenery and vibrant flowers.

Pier Blue Inn Old Saybrook - Essex

2.0 star property
7.8 out of 10, Good, (1001)
"Nice, clean and friendly. "
The price is AU$141
includes taxes & fees
27 July - 28 July
Pier Blue Inn Old Saybrook - Essex
Clinton Motel
Situated in a landscaped area, this single-story building offers a convenient parking space.

Clinton Motel

2.5 star property
8.6 out of 10, Excellent, (259)
"Great and quiet stay, friendly owners, just right! "
The price is AU$154
includes taxes & fees
27 July - 28 July
Clinton Motel
Cliffside Resort Condominiums
Stunning beachfront residential area with multi-story buildings and a central park.

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (228)
"After some lengthy travel to get to LI this was an excellent choice to start our vacation. Great accommodations, comfortable and great location. "
The price is AU$653
includes taxes & fees
27 July - 28 July
Cliffside Resort Condominiums
Sea Crest Resort
Enjoy the serene beach view from this balcony, featuring a round table and two chairs.

Sea Crest Resort

2.5 star property
9.2 out of 10, Wonderful, (459)
"Great stay and beautiful clean room "
The price is AU$802
includes taxes & fees
27 July - 28 July
Sea Crest Resort
East Hampton Art House Bed & Breakfast
Relax in a spacious outdoor area with a swimming pool surrounded by gardens and seating arrangements.

East Hampton Art House Bed & Breakfast

4.0 star property
9.6 out of 10, Exceptional, (63)
"Very profesional, very good experiencia , the host the best , the property beatiful 100 porcent recomended"
The price is AU$1,597
includes taxes & fees
5 Aug - 6 Aug
East Hampton Art House Bed & Breakfast
Sag Harbor Inn
Relax by the rectangular pool surrounded by a tiled deck and lounge chairs.

Sag Harbor Inn

3.5 star property
9.4 out of 10, Exceptional, (534)
"Great place to stay!"
The price is AU$837
includes taxes & fees
10 Aug - 11 Aug
Sag Harbor Inn
The Captain Stannard
Cozy up by the fireplace in this stylish living room, featuring a comfortable sofa, armchair, and decorative artwork.

The Captain Stannard

3.0 star property
9.6 out of 10, Exceptional, (233)
"Everything was fantastic, will stay again!"
The Captain Stannard
Liberty Inn
Stroll through the serene garden, surrounded by lush greenery and a tranquil water feature.

Liberty Inn

2.0 star property
7.4 out of 10, Good, (610)
"Great property owner…Clean and well located for the Old Saybrook area…"
The price is AU$153
includes taxes & fees
5 Aug - 6 Aug
Liberty Inn
Canoe Place Inn and Cottages
Relax in a serene outdoor setting with a covered patio, decorative water feature, and traditional architecture.

Canoe Place Inn and Cottages

4.0 star property
10.0 out of 10, Exceptional, (47)
"Wonderful stay! "
Canoe Place Inn and Cottages
The Harbor Front Inn
Enjoy a variety of hot beverages at our coffee bar, featuring coffee, decaf, and hot water options.

The Harbor Front Inn

3.5 star property
8.8 out of 10, Excellent, (491)
"Great location wonderful breakfast selections "
The price is AU$704
includes taxes & fees
27 July - 28 July
The Harbor Front Inn
The Pridwin Hotel
Relax by the calm pool, surrounded by comfortable sun loungers and shaded areas.

The Pridwin Hotel

4.0 star property
9.4 out of 10, Exceptional, (66)
"Lovely hotel/ resort. Look forward to going again!"
The Pridwin Hotel
Wainscott Woods Retreat
Exterior

Wainscott Woods Retreat

2.0 star property
10.0 out of 10, Exceptional, (1)
"HIDDEN GEM IN THE HEART OF HAMPTONS! What a special place to stay in the Hamptons! I am so happy we found this wonderful gem! This hotel is clean, quiet and well managed. The pool is beautiful the rooms are modern, sleek and clean! The grounds are beautifully manicured. The location is perfect! This new hotel has the charm of a bed and breakfast. The hotel is a short car ride from either East Hampton or Southampton which is perfect if you chose to explore all the little towns the Hampton's has...
The price is AU$2,040
includes taxes & fees
27 July - 28 July
Wainscott Woods Retreat
Sound View Greenport
Relax by the serene pool surrounded by lounge chairs and umbrellas.

Sound View Greenport

4.0 star property
8.4 out of 10, Very good, (541)
"The water views of the Sound were spectacular & were accessible for every meal. The staff was friendly & accommodating -- they had lots of good meal recommendations both in house & for outside restaurants. This inn had a very peaceful vibe -- would definitely return!"
The price is AU$886
includes taxes & fees
21 Aug - 22 Aug
Sound View Greenport
Hampton's Vacation Inn
Enjoy cooking in this well-equipped kitchen with a dishwasher, coffee maker, and stainless steel appliances.

Hampton's Vacation Inn

2.5 star property
9.0 out of 10, Wonderful, (292)
"The location was great. The room was beautiful. The grounds were beautiful. Had a great time."
The price is AU$604
includes taxes & fees
24 July - 25 July
Hampton's Vacation Inn
Water's Edge Resort & Spa
Experience the hotel's elegant design and unwind by the spacious pool surrounded by lounge chairs.

Water's Edge Resort & Spa

3.5 star property
8.8 out of 10, Excellent, (1000)
"Grounds are beautiful. Good food and staff. One down side are the bed pillows- all were toooo big and puffy- so uncomfortable! "
The price is AU$551
includes taxes & fees
27 July - 28 July
Water's Edge Resort & Spa
Quality Inn Old Saybrook - Westbrook
Relax by the oval-shaped pool surrounded by lounge chairs and a high ceiling with a grid-like pattern.

Quality Inn Old Saybrook - Westbrook

2.5 star property
7.6 out of 10, Good, (1007)
"Great location and pool, close to a wonderful restaurant "
The price is AU$194
includes taxes & fees
4 Aug - 5 Aug
Quality Inn 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.

Our guide on where to stay in The Heights

Find the best The Heights areas for the activities you enjoy most.
Hay Beach map

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

The Atlantic Hotel

The Atlantic Hotel

10/10 Excellent
"great stay "
Chandradat 1-night trip
Posted 22 hours ago
The Atlantic Hotel

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. Another top choice in the area is The Chequit.

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 14 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.