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Find hotels in The Heights, Shelter Island Heights from $404

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Discover 4,066 The Heights hotels and places to stay, with room rates, reviews, and availability. Most hotels are fully refundable.

The Chequit
Outdoor dining

The Chequit

3.0 star property
8.8 out of 10, Excellent, (29)
"Prefect place for a staycation "
$604 nightly
The price is $690
Jul 7 - Jul 8
Total includes taxes and fees
The Chequit
Driftwood Resort
Apartment, 1 Bedroom | Private kitchen | Fridge, microwave, cookware/dishes/utensils

Driftwood Resort

3.5 star property
9.0 out of 10, Wonderful, (225)
"Phenomenal property and our room had a private sand patio. Service was extremely attentive and friendly. The beach was very spacious and pretty clean."
$426 nightly
The price is $486
Jul 7 - Jul 8
Total includes taxes and fees
Driftwood Resort
Sea Crest Resort
Studio Unit Upper Oceanfront 'San Remo' | Terrace/patio

Sea Crest Resort

2.5 star property
9.2 out of 10, Wonderful, (458)
"Lovely place !!"
$387 nightly
The price is $442
Jul 7 - Jul 8
Total includes taxes and fees
Sea Crest Resort
The Hermitage
Seasonal outdoor pool

The Hermitage

3.5 star property
9.2 out of 10, Wonderful, (158)
"Quiet peaceful beautiful "
$613 nightly
The price is $700
Jul 10 - Jul 11
Total includes taxes and fees
The Hermitage
Ocean Vista Resort
View from property

Ocean Vista Resort

2.5 star property
9.0 out of 10, Wonderful, (178)
"Nice place to stay out on the east end"
$465 nightly
The price is $531
Jul 7 - Jul 8
Total includes taxes and fees
Ocean Vista Resort
Windward Shores Ocean Resort
View from property

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (286)
"Easy checking in and out Easy access few steps to beach from first floor unit "
$354 nightly
The price is $404
Jul 9 - Jul 10
Total includes taxes and fees
Windward Shores Ocean Resort
The Roundtree, Amagansett
Beach nearby, white sand, sun loungers, beach umbrellas

The Roundtree, Amagansett

4.5 star property
9.8 out of 10, Exceptional, (88)
"The Roundtree was one of the most peaceful hotels we’ve ever stayed in. I highly recommend for a romantic getaway. "
$1,360 nightly
The price is $1,554
Jul 7 - Jul 8
Total includes taxes and fees
The Roundtree, Amagansett
The Reform Club
Deluxe Suite | 1 bedroom, Egyptian cotton sheets, premium bedding, down comforters

The Reform Club

2.0 star property
10.0 out of 10, Exceptional, (2)
"Unique property; lots of attention from staff; close to town."
$1,750 nightly
The price is $1,999
Jul 7 - Jul 8
Total includes taxes and fees
The Reform Club
Journey East Hampton
Exterior

Journey East Hampton

4.0 star property
9.0 out of 10, Wonderful, (139)
"We had a good stay at The Journey. Can’t wait to come back! "
$408 nightly
The price is $467
Jul 9 - Jul 10
Total includes taxes and fees
Journey East Hampton
East Hampton House Resort
Deluxe Studio | Living area | TV

East Hampton House Resort

3.0 star property
9.0 out of 10, Wonderful, (264)
"Great "
$381 nightly
The price is $435
Jul 7 - Jul 8
Total includes taxes and fees
East Hampton House Resort
Mill House Inn
Front of property - evening/night

Mill House Inn

5.0 star property
9.0 out of 10, Wonderful, (69)
"Great experience at a wonderful property!"
$1,095 nightly
The price is $1,250
Jul 7 - Jul 8
Total includes taxes and fees
Mill House Inn
East Hampton Art House Bed & Breakfast
Aerial view

East Hampton Art House Bed & Breakfast

4.0 star property
9.6 out of 10, Exceptional, (61)
"The hosts were really nice and the breakfast is excellent!"
$1,018 nightly
The price is $1,163
Jul 9 - Jul 10
Total includes taxes and fees
East Hampton Art House Bed & Breakfast
The Huntting Inn
Standard Room, 1 King Bed | 1 bedroom, iron/ironing board, free WiFi, bed sheets

The Huntting Inn

3.5 star property
8.8 out of 10, Excellent, (90)
"Best place to stay in East Haven! Location is perfect, attention can’t "
$588 nightly
The price is $670
Aug 3 - Aug 4
Total includes taxes and fees
The Huntting Inn
The 1770 House Restaurant & Inn
Reception

The 1770 House Restaurant & Inn

4.0 star property
9.8 out of 10, Exceptional, (155)
"We had a fantastic stay!!! Thank you "
$543 nightly
The price is $707
Jul 7 - Jul 8
Total includes taxes and fees
The 1770 House Restaurant & Inn
The Hedges Inn
Room One: Large Queen Guestroom | Egyptian cotton sheets, premium bedding, in-room safe

The Hedges Inn

3.5 star property
9.6 out of 10, Exceptional, (68)
"Absolutely fabulous homely and beautifully decorated Conveniently located between downtown and the beach so easy to walk"
$842 nightly
The price is $962
Jul 7 - Jul 8
Total includes taxes and fees
The Hedges Inn
The Maidstone
Front of property - evening/night

The Maidstone

4.0 star property
8.0 out of 10, Very Good, (139)
"The details in this beautiful spot is what makes it so special and magical. "
$825 nightly
The price is $943
Jul 15 - Jul 16
Total includes taxes and fees
The Maidstone
EHP Resort & Marina
Boating

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. "
$591 nightly
The price is $675
Jul 9 - Jul 10
Total includes taxes and fees
EHP Resort & Marina
The Sagaponack
Exterior

The Sagaponack

3.0 star property
8.8 out of 10, Excellent, (160)
"The location was great, the room was clean, and the staff were very friendly and accommodating."
$388 nightly
The price is $444
Jul 8 - Jul 9
Total includes taxes and fees
The Sagaponack
A Room At The Beach
Outdoor pool

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!"
$770 nightly
The price is $880
Jul 7 - Jul 8
Total includes taxes and fees
A Room At The Beach
Topping Rose House
Outdoor pool

Topping Rose House

4.5 star property
9.2 out of 10, Wonderful, (133)
"Had an excellent stay at Topping Rose House! Can’t wait to be back soon!"
$1,382 nightly
The price is $1,582
Jul 8 - Jul 9
Total includes taxes and fees
Topping Rose House
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 and neighborhoods for the activities you enjoy most.
Hay Beach map

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.

Frequently asked questions

What are the best hotels in The Heights that travelers recommend?
The Chequit stands out as a top choice in Shelter Island Heights, boasting an impressive traveler review score of 8.8. This charming hotel combines a rustic vibe with modern comforts, making it an inviting retreat for all types of travelers. Guests love its premium bedding and Frette Italian sheets, ensuring a restful night's sleep after a day of adventure. With free Wi-Fi and free self-parking, convenience is at the forefront of your stay, allowing you to focus on enjoying everything the area has to offer.
What are the best family hotels in The Heights?
The Chequit, located in the charming Shelter Island Heights, is an inviting family-friendly hotel that promises a delightful stay for guests of all ages. Rated 8.8 by travelers, this property offers connecting rooms, making it easier for families to stay close together while enjoying their own space.
What are the best budget hotels in The Heights?
The Chequit, located in the charming Shelter Island Heights, is a delightful option for budget-conscious travelers seeking a cozy retreat. With an excellent review score of 8.8, this hotel boasts free WiFi in rooms, ensuring you stay connected during your getaway, and premium bedding with Frette Italian sheets for a luxurious night's sleep.
Can I cancel my hotel reservation on Expedia?
Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline -- this is often within 24-48 hours of your scheduled arrival. If you have a non-refundable booking, it might still be possible to receive a refund if you cancel it within 24 hours of booking. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use our "Fully refundable property" filter during your search to find the right The Heights hotel for you.
How can I save on a The Heights hotel booking with Expedia?
With Expedia, you earn OneKeyCash™* on eligible The Heights hotel bookings for every dollar you spend -- just join our One Key™ travel rewards program to get started. It's free to join, and you'll unlock our lowest Member Prices as soon as you're signed in. On top of this, you could also save significantly by bundling your hotel and flights together on Expedia.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
How much is the nightly rate at a The Heights hotel?
Hotel prices in The Heights often vary, but you can find a great deal from $404 on Expedia. Different factors affect nightly hotel rates, such as the time of year or the days of the week you want to book. To find the best deals for your stay, be flexible with your dates, and sort search results by "Price: low to high" for our cheapest rates.