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The Heights Hotels, Shelter Island Heights

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Check prices for these dates

Tonight
4 Aug - 5 Aug
Tomorrow
5 Aug - 6 Aug
This weekend
8 Aug - 10 Aug
Next weekend
15 Aug - 17 Aug

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4021 Cheap Hotels in The Heights - Specials, Reviews, & Last Minute Deals

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, (32)
"we loved it!"
The Chequit
Driftwood Resort
Enjoy cooking in this well-equipped kitchen with a tiled backsplash and black refrigerator.

Driftwood Resort

3.5 star property
9.0 out of 10, Wonderful, (227)
"Phenomenal property and our room had a private sand patio. Service was extremely attentive and friendly. The beach was very spacious and pretty clean."
The price is NZ$533
includes taxes & fees
3 Sept - 4 Sept
Driftwood Resort
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, (467)
"Great stay and beautiful clean room "
The price is NZ$571
includes taxes & fees
4 Sept - 5 Sept
Sea Crest Resort
The Hermitage
Relax by the resort's central pool surrounded by lounge chairs and umbrellas, offering stunning views of the sea.

The Hermitage

3.5 star property
9.2 out of 10, Wonderful, (159)
"Quiet peaceful beautiful "
The price is NZ$1,482
includes taxes & fees
5 Aug - 6 Aug
The Hermitage
Ocean Vista Resort
Guests can enjoy access to the beach and scenic ocean views.

Ocean Vista Resort

2.5 star property
9.0 out of 10, Wonderful, (183)
"It waa great for traveling with kids. Close to the beach and my kids loved the indoor pool!"
Ocean Vista Resort
Windward Shores Ocean Resort
Enjoy a panoramic ocean view from the comfort of this room, featuring a dining table, seating area, and sliding glass doors to the outdoor patio.

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (289)
"Easy checking in and out Easy access few steps to beach from first floor unit "
The price is NZ$567
includes taxes & fees
2 Sept - 3 Sept
Windward Shores Ocean Resort
The Roundtree, Amagansett
Enjoy a leisurely ride along the beach, where the ocean meets the shore.

The Roundtree, Amagansett

4.5 star property
9.8 out of 10, Exceptional, (89)
"The Roundtree was one of the most peaceful hotels we’ve ever stayed in. I highly recommend for a romantic getaway. "
The price is NZ$2,625
includes taxes & fees
12 Aug - 13 Aug
The Roundtree, Amagansett
The Reform Club
Relax in a spacious bedroom with a large bed, high ceiling, and natural light pouring in through the skylight.

The Reform Club

2.0 star property
10.0 out of 10, Exceptional, (2)
"Unique property; lots of attention from staff; close to town."
The Reform Club
Journey East Hampton
Stylish building with a brick and white exterior, featuring large windows and a covered outdoor area with a deck and potted plants.

Journey East Hampton

4.0 star property
9.2 out of 10, Wonderful, (143)
"We had a good stay at The Journey. Can’t wait to come back! "
The price is NZ$984
includes taxes & fees
1 Sept - 2 Sept
Journey East Hampton
East Hampton House Resort
Enjoy a restful stay in this stylish room with a comfortable bed, bedside table, and balcony offering a view of lush greenery.

East Hampton House Resort

3.0 star property
9.0 out of 10, Wonderful, (271)
"The place was very well groomed and the early check in notification by text was unexpected and very much welcomed. That made the experience great from the beginning. Very nice flowers and clean pool"
The price is NZ$699
includes taxes & fees
2 Sept - 3 Sept
East Hampton House Resort
Mill House Inn
Stately home surrounded by lush greenery and mature trees, offering a serene and atmosphere.

Mill House Inn

5.0 star property
9.0 out of 10, Wonderful, (70)
"Great experience at a wonderful property!"
The price is NZ$2,113
includes taxes & fees
10 Aug - 11 Aug
Mill House Inn
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 NZ$1,324
includes taxes & fees
2 Sept - 3 Sept
East Hampton Art House Bed & Breakfast
The Huntting Inn
Relax in style on the patio, surrounded by lush greenery and comfortable seating.

The Huntting Inn

3.5 star property
8.8 out of 10, Excellent, (95)
"Great property."
The price is NZ$1,133
includes taxes & fees
26 Aug - 27 Aug
The Huntting Inn
The 1770 House Restaurant & Inn
Stroll through the serene garden, lined with lush greenery and vibrant flowers, to a historic building with a decorative facade.

The 1770 House Restaurant & Inn

4.0 star property
9.8 out of 10, Exceptional, (157)
"The staff was incredibly genuine and the property felt intimate and comfortable."
The price is NZ$1,328
includes taxes & fees
25 Aug - 26 Aug
The 1770 House Restaurant & Inn
The Hedges Inn
Cozy retreat with a four-poster bed, dresser, and nightstand, plus a large mirror and TV for a comfortable stay.

The Hedges Inn

3.5 star property
9.6 out of 10, Exceptional, (70)
"Great staff "
The price is NZ$1,819
includes taxes & fees
5 Aug - 6 Aug
The Hedges Inn
The Maidstone
Stunning traditional building with a beautifully lit entrance and lush surroundings.

The Maidstone

4.0 star property
8.0 out of 10, Very good, (141)
"The details in this beautiful spot is what makes it so special and magical. "
The Maidstone
EHP Resort & Marina
Experience serene waterfront views and tranquil boating opportunities from the marina.

EHP Resort & Marina

3.5 star property
7.8 out of 10, Good, (8)
"Rooms are well appointed with cozy cottage vibe yet modern and clean . My only ask would be rooms should have one full length mirror. The property is beautiful, location amazing. "
The price is NZ$1,387
includes taxes & fees
1 Sept - 2 Sept
EHP Resort & Marina
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 NZ$2,259
includes taxes & fees
10 Aug - 11 Aug
Wainscott Woods Retreat
The Sagaponack
Relax in a serene outdoor space surrounded by lush greenery and a charming house with a gabled roof.

The Sagaponack

3.0 star property
8.8 out of 10, Excellent, (165)
"The location was great, the room was clean, and the staff were very friendly and accommodating."
The price is NZ$727
includes taxes & fees
1 Sept - 2 Sept
The Sagaponack
A Room At The Beach
Relax by the pool surrounded by lush greenery and shaded by three umbrellas.

A Room At The Beach

3.0 star property
9.0 out of 10, Wonderful, (84)
"Beautiful property and amazing staff, I will definitely be back soon!"
The price is NZ$1,168
includes taxes & fees
1 Sept - 2 Sept
A Room At The Beach
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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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

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

10/10 Excellent
"The room was beautiful-clean, spacious and a great view!! I would say that the prices for in-room amenities were a bit steep however. "
Linda 3-night trip
Posted 13 hours ago
Saybrook Point Resort & Marina

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.