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The Heights Hotels near Shelter Island Heights

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Check prices for these dates

Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29

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Our top choices for The Heights hotels

An outdoor patio area with string lights, tables, chairs, and a fire pit.

1. The Chequit

The Chequit
3.0 star property
The Heights
9.0 out of 10, Wonderful, (78 reviews)
"We enjoyed our stay!"
Australia
Nicholas
The price is P11,471
P13,105 total
includes taxes & fees
Nov 15 - Nov 16
The Chequit
A conservatory with a dining table set for four, surrounded by wooden chairs, with a view of trees and a lawn.

2. House on Chase Creek

House on Chase Creek
2.5 star property
The Heights
9.4 out of 10, Exceptional, (87 reviews)
"Such a cute place to stay! Bill was super kind and helpful! I was only in for a quick night but I would definitely stay here again!!"
United States
Tracey
The price is P11,773
P13,450 total
includes taxes & fees
Nov 17 - Nov 18
House on Chase Creek
The entrance to The Harbor Front Inn with a double door and the address number 209.

3. The Harbor Front Inn

The Harbor Front Inn
3.5 star property
2.4 km from The Heights
9.0 out of 10, Wonderful, (676 reviews)
"Clean and comfortable room. Great location to walk around town. Nice continental breakfast."
United States
Jessika
The price is P8,613
P11,660 total
includes taxes & fees
Dec 13 - Dec 14
The Harbor Front Inn
A rooftop deck with outdoor seating, fire pits, and a view of a body of water.

4. The Menhaden

The Menhaden
3.5 star property
2.4 km from The Heights
9.6 out of 10, Exceptional, (197 reviews)
"Very clean, excellent staff and excellent location. All of the shops and restaurants are within walking distance, and the wineries a very short cab ride. Really enjoyed staying here and we will absolutely be back."
United States
Daniel
The price is P16,207
P21,384 total
includes taxes & fees
Dec 13 - Dec 14
The Menhaden
A wooden pathway leading to beach chairs and umbrellas, surrounded by lush greenery and a view of the sea.

5. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
2.3 km from The Heights
10.0 out of 10, Exceptional, (193 reviews)
"Amazing place to stay with a great location. We will definitely be back!"
United States
Kathleen
The price is P14,010
P16,008 total
includes taxes & fees
Dec 6 - Dec 7
Silver Sands Motel & Beach Bungalows
A two-story house with a balcony, outdoor seating area, and a variety of plants.

6. Zey Hotel

Zey Hotel
3.5 star property
2.7 km from The Heights
9.2 out of 10, Wonderful, (449 reviews)
"Great place to stay for a walkable visit to Greenport NY. Comfy bed, great rooms for hanging out, close to everything."
United States
JoAnn
The price is P10,317
P11,787 total
includes taxes & fees
Nov 17 - Nov 18
Zey Hotel
A cozy interior with a bar area, seating, and a fireplace.

7. Oyster Estate

Oyster Estate
4.0 star property
2.5 km from The Heights
9.2 out of 10, Wonderful, (302 reviews)
"convenient location, clean & updated room. great stay :)"
United States
Jacqueline
The price is P11,471
P14,452 total
includes taxes & fees
Dec 2 - Dec 3
Oyster Estate
A pathway flanked by lush greenery and bamboo, leading to a building with a wooden exterior.

8. American Beech Hotel

American Beech Hotel
3.5 star property
2.6 km from The Heights
9.0 out of 10, Wonderful, (208 reviews)
"Great location, very friendly and helpful "
United States
Mary
The price is P15,208
P19,922 total
includes taxes & fees
Nov 18 - Nov 19
American Beech Hotel
A spacious room with wicker furniture, large windows, and a view of the sea.

9. Sound View Greenport

Sound View Greenport
4.0 star property
3.8 km from The Heights
8.4 out of 10, Very good, (768 reviews)
"The ambience is amazing! We loved our stay!!"
United States
Christine
The price is P9,479
P12,650 total
includes taxes & fees
Dec 14 - Dec 15
Sound View Greenport
A modern outdoor seating area with two wicker chairs and a small table, overlooking a body of water and a wooden deck.

10. 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, (351 reviews)
"The shoals was a perfect place for our north fork adventures. The staff was very friendly and extremely accommodating! The location was beautiful and very relaxing."
United States
William
The price is P11,813
P15,088 total
includes taxes & fees
Nov 22 - Nov 23
The Shoals Suites and Slips
A balcony with a view of the ocean, a lawn, and a house in the background.

11. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
3.5 km from The Heights
9.0 out of 10, Wonderful, (300 reviews)
"Great condo. Very nice location and grounds."
United States
William
The price is P12,233
P21,042 total
includes taxes & fees
Nov 26 - Nov 27
Cliffside Resort Condominiums
A modern house with a deck, outdoor seating, and a fire pit.

12. North Fork Resort

North Fork Resort
3.0 star property
3.4 km from The Heights
9.6 out of 10, Exceptional, (73 reviews)
"Everything was perfect 💞"
United States
Altynai
The price is P20,462
P23,377 total
includes taxes & fees
Nov 24 - Nov 25
North Fork Resort
A waterfront property with a large house, multiple boats docked, and lush greenery.

13. Sag Harbor Inn

Sag Harbor Inn
3.5 star property
10 km from The Heights
9.4 out of 10, Exceptional, (689 reviews)
"The room was nicely appointed; sufficient parking; close to downtown; and a nice variety for breakfast."
United States
Annie
The price is P13,947
P15,934 total
includes taxes & fees
Nov 15 - Nov 16
Sag Harbor Inn
A two-story white house with a porch and an American flag.

14. Seven - A Resort Style Inn

Seven - A Resort Style Inn
2.0 star property
0.8 km from The Heights
The price is P24,260
P27,718 total
includes taxes & fees
Nov 20 - Nov 21
Seven - A Resort Style Inn
A pool area with umbrellas, potted plants, and a pathway leading to a building.

15. Faraway Sag Harbor

Faraway Sag Harbor
4.0 star property
10.1 km from The Heights
9.0 out of 10, Wonderful, (322 reviews)
"Great location , wonderful lobby bar Cute rooms"
United States
Thomas
The price is P19,787
P24,867 total
includes taxes & fees
Dec 6 - Dec 7
Faraway Sag Harbor
A large hotel with a spacious outdoor patio area, multiple dining tables, and umbrellas.

16. Water's Edge Resort & Spa

Water's Edge Resort & Spa
3.5 star property
23.3 km from The Heights
9.0 out of 10, Wonderful, (1,003 reviews)
"It was a lovely property and close to stores and places to eat."
United States
ERIKA
The price is P8,485
P10,856 total
includes taxes & fees
Nov 23 - Nov 24
Water's Edge Resort & Spa
A modern building with a pool, featuring a dining area with tables and chairs, and a glass entrance.

17. Topping Rose House

Topping Rose House
4.5 star property
16.5 km from The Heights
9.0 out of 10, Wonderful, (165 reviews)
"Incredible stay. Going back in the fall"
United States
Adam
The price is P39,834
P45,734 total
includes taxes & fees
Nov 27 - Nov 28
Topping Rose House
Living area

18. East Hampton House Resort

East Hampton House Resort
3.0 star property
20.1 km from The Heights
9.0 out of 10, Wonderful, (354 reviews)
"The room was spacious and clean and the balcony was lovely. Would love to return at a different time of the year when the grounds could be better appreciated. It is in a great location between East Hampton and Amagansett with plenty of dining options."
United States
Frederica
The price is P8,836
P11,827 total
includes taxes & fees
Nov 19 - Nov 20
East Hampton House Resort
A modern bathroom with a large mirror, wooden vanity, and a sink. There is a chair and a small table in the adjacent living area, with a sofa and a view of the outdoors.

19. The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
22.6 km from The Heights
9.6 out of 10, Exceptional, (619 reviews)
"great spot to stay,"
United States
Armando
The price is P7,514
P8,585 total
includes taxes & fees
Nov 23 - Nov 24
The Bentley Hotel Southampton
Restaurant

20. Southampton Inn

Southampton Inn
3.0 star property
22 km from The Heights
8.6 out of 10, Excellent, (604 reviews)
"First time staying there, loved it. Great location, shuttle to beach, good times!"
United States
Kevin
The price is P12,737
P15,589 total
includes taxes & fees
Nov 22 - Nov 23
Southampton Inn
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.
View all properties

Compare popular hotels in The Heights

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet-friendly
WiFi included
A conservatory with a dining table set for four, surrounded by wooden chairs, with a view of trees and a lawn.
House on Chase Creek
2.5 star property
9.4
Exceptional
87 reviews
View
An outdoor patio area with string lights, tables, chairs, and a fire pit.
The Chequit
3.0 star property
9.0
Wonderful
78 reviews
View
A wooden pathway leading to beach chairs and umbrellas, surrounded by lush greenery and a view of the sea.
Silver Sands Motel & Beach Bungalows
4.0 star property
10.0
Exceptional
193 reviews
View
A rooftop deck with outdoor seating, fire pits, and a view of a body of water.
The Menhaden
3.5 star property
9.6
Exceptional
197 reviews
View
The entrance to The Harbor Front Inn with a double door and the address number 209.
The Harbor Front Inn
3.5 star property
9.0
Wonderful
676 reviews
View

Where to stay in The Heights

Find the best The Heights areas and neighborhoods for the activities you enjoy most.
A calm lake with reflections of clouds, surrounded by trees and a distant structure.

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

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

8/10 Good
"The location of this hotel was excellent. It is close to many restaurants. Easy to get an Uber/Lyft. The clerk at the reception was knowledgeable and friendly. The room was clean. The breakfast was good. The hotel needs some updating which they are in the process of doing and that is why I gave it 4 stars overall."
Kerry 1-night trip
Posted 5 hours ago
Quality Inn Old Saybrook - Westbrook

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 our traveler data, The Chequit is one of the top choices for your stay in The Heights. This hotel offers a restaurant and free parking.
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 12 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.
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.

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