The Best Hotels in The Heights, Shelter Island Heights - 2026 Updated Prices | Expedia

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The Heights
Shelter Island Heights
New York
Hotels
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Holiday Rentals in Shelter Island Heights The Heights Car Hire The Heights Holidays

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Our top choices for The Heights hotels

A serene landscape with a calm body of water reflecting trees with autumn foliage.

A conservatory with a dining table set for four, surrounded by wooden chairs, with a view of trees and a lawn.

A sign for 'House on Chase Creek' with a duck illustration.

A serene lakeside view with two Adirondack chairs facing a calm lake, surrounded by trees and a clear sky.

1. House on Chase Creek

House on Chase Creek

2.5 star property

The Heights

9.4 out of 10, Exceptional, (86 reviews)

9.4/10

Exceptional

(86 reviews)

"Nice owner.. convenient location"

"Nice owner.. convenient location"

United States

Calvin

The price is 5.597.280 ₫

5.597.280 ₫

6.394.960 ₫ total

includes taxes & fees

5 Oct - 6 Oct

House on Chase Creek

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

A large, white building with multiple windows and a prominent tree in the foreground.

A staircase with wooden balusters and a white wall.

A modern hotel room with a large bed, a sofa, a chair, a small table, and a mirror.

2. The Chequit

3.0 star property

The Heights

9.2 out of 10, Wonderful, (62 reviews)

9.2/10

Wonderful

(62 reviews)

"It’s a beautiful property with a fun bar and delicious restaurant . The rooms were beautiful and the bed was super comfortable"

"It’s a beautiful property with a fun bar and delicious restaurant . The rooms were beautiful and the bed was super comfortable"

United States

Kristin

The price is 5.382.000 ₫

5.382.000 ₫

6.148.935 ₫ total

includes taxes & fees

4 Oct - 5 Oct

3. Shelter Island House

Shelter Island House

3.5 star property

0.9 km from The Heights

8.4 out of 10, Very good, (66 reviews)

8.4/10

Very good

(66 reviews)

"This boutique hotel is a true gem. Set among lush trees and beautiful landscaping, and with excellent indoor space, it provides a welcoming and relaxing atmosphere."

"This boutique hotel is a true gem. Set among lush trees and beautiful landscaping, and with excellent indoor space, it provides a welcoming and relaxing atmosphere."

United States

Dorothy

The price is 5.232.500 ₫

5.232.500 ₫

5.977.920 ₫ total

includes taxes & fees

5 Oct - 6 Oct

Shelter Island House

A rooftop terrace with lounge chairs, a wooden table, and a view of the landscape.

A hotel room with a bed, a blue sofa, a wicker chair, a small table with a vase, and a lamp.

A large building with multiple floors, surrounded by a residential area with houses and a body of water.

A wooden pier extending into a body of water with a cloudy sky above.

4. The Harbor Front Inn

The Harbor Front Inn

3.5 star property

2.4 km from The Heights

9.0 out of 10, Wonderful, (659 reviews)

9.0/10

Wonderful

(659 reviews)

"Great location"

"Great location"

United States

Jordan

The price is 5.826.600 ₫

5.826.600 ₫

7.399.449 ₫ total

includes taxes & fees

25 Oct - 26 Oct

The Harbor Front Inn

A seaside dining area with tables, chairs, and umbrellas, overlooking a body of water.

A beach with sun loungers and umbrellas, a sandy path, and a view of the water.

A room with a bed, two wicker chairs with checkered cushions, a small round table with a vase of flowers, and a view of a lake through a window with a bamboo blind.

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, (170 reviews)

10/10

Exceptional

(170 reviews)

"Excellent stay. The room was clean and stylish. Can’t wait to come back"

"Excellent stay. The room was clean and stylish. Can’t wait to come back"

United States

Sarah

The price is 8.450.000 ₫

8.450.000 ₫

9.654.320 ₫ total

includes taxes & fees

12 Oct - 13 Oct

Silver Sands Motel & Beach Bungalows

A bedroom with a bed, bedside tables, a lamp, a window, and a door.

A beach with a wooden walkway along the shore, calm water, and a sunset sky.

A living room with a beige sofa, a coffee table, and a dining table set with plates and glasses.

A large, light blue two-story house with a steep roof, surrounded by greenery and a gravel driveway.

6. West Neck Guesthouse

West Neck Guesthouse

3.5 star property

0.6 km from The Heights

8.2 out of 10, Very good, (46 reviews)

8.2/10

Very good

(46 reviews)

"It was great! The location was perfect, plenty of amenities close by as well. Easy ferry access depending on time of day. Room was very clean. Will be staying again!"

"It was great! The location was perfect, plenty of amenities close by as well. Easy ferry access depending on time of day. Room was very clean. Will be staying again!"

United States

Allie

The price is 8.151.000 ₫

8.151.000 ₫

9.312.680 ₫ total

includes taxes & fees

1 Oct - 2 Oct

West Neck Guesthouse

A cozy interior with a bar area, seating, and a fireplace.

A poolside area with lounge chairs and yellow umbrellas.

A bedroom with a large bed, bedside tables, a window with curtains, and wooden shelving with various items.

A modern outdoor seating area with a sofa, cushions, a wooden coffee table with a fire feature, and a decorative wall with geometric patterns.

7. Oyster Estate

4.0 star property

2.5 km from The Heights

9.2 out of 10, Wonderful, (291 reviews)

9.2/10

Wonderful

(291 reviews)

"Clean, great amenities, and friendly staff!"

"Clean, great amenities, and friendly staff!"

United States

Elizabeth

The price is 8.216.000 ₫

8.216.000 ₫

10.351.641 ₫ total

includes taxes & fees

5 Oct - 6 Oct

A two-story house with a balcony, outdoor seating area, and a variety of plants.

A bar area with stools, a shelf with glasses, and decorative plants.

A restaurant with a signboard listing its hours of operation.

A bathroom with a bathtub, green tiled walls, and windows with white blinds.

8. Zey Hotel

3.5 star property

2.7 km from The Heights

9.2 out of 10, Wonderful, (409 reviews)

9.2/10

Wonderful

(409 reviews)

"Great location…thoroughly enjoyed our time."

"Great location…thoroughly enjoyed our time."

United States

Renee

The price is 4.387.500 ₫

4.387.500 ₫

5.012.721 ₫ total

includes taxes & fees

27 Sept - 28 Sept

A modern building entrance with a black and white striped awning, a staircase leading inside, and two bicycles parked outside.

A modern bar area with black bar stools, a counter with a variety of bottles, and hanging green plants in wire baskets.

A rooftop deck with outdoor seating, fire pits, and a view of a body of water.

A modern living room with a grey sofa, black and white patterned rug, and a coffee table.

9. The Menhaden

3.5 star property

2.4 km from The Heights

9.6 out of 10, Exceptional, (191 reviews)

9.6/10

Exceptional

(191 reviews)

"Staff was very accommodating and extremely nice, Great stay!"

"Staff was very accommodating and extremely nice, Great stay!"

United States

Lisa

The price is 8.671.520 ₫

8.671.520 ₫

10.947.040 ₫ total

includes taxes & fees

29 Sept - 30 Sept

A modern outdoor seating area with two wicker chairs and a small table, overlooking a body of water and a wooden deck.

A modern hotel room with a bed, a sofa, a coffee table, and a view of the city.

A modern living room with a blue sofa, light blue armchairs, a dining table, and a kitchen in the background.

A light blue bus with "THE SHOALS" written on the front, parked in a driveway with a house and garden in the background.

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, (342 reviews)

9.4/10

Exceptional

(342 reviews)

"Loved everything about our stay!"

"Loved everything about our stay!"

United States

Melissa

The price is 5.247.450 ₫

5.247.450 ₫

6.645.211 ₫ total

includes taxes & fees

1 Oct - 2 Oct

The Shoals Suites and Slips

A pathway flanked by lush greenery and bamboo, leading to a building with a wooden exterior.

An outdoor dining area with tables and chairs, string lights, and hanging lanterns.

A modern lounge area with a curved sofa, round coffee tables, and a large potted plant.

A reception desk with a white backdrop, surrounded by various plants and a modern pendant light.

11. American Beech Hotel

American Beech Hotel

3.5 star property

2.6 km from The Heights

9.0 out of 10, Wonderful, (207 reviews)

9.0/10

Wonderful

(207 reviews)

"Great location, very friendly and helpful "

"Great location, very friendly and helpful "

United States

Mary

The price is 5.954.000 ₫

5.954.000 ₫

7.842.640 ₫ total

includes taxes & fees

1 Oct - 2 Oct

American Beech Hotel

12. Cliffside Resort Condominiums

Cliffside Resort Condominiums

3.0 star property

3.5 km from The Heights

9.0 out of 10, Wonderful, (294 reviews)

9.0/10

Wonderful

(294 reviews)

"Great place!"

"Great place!"

United States

Christine

The price is 7.183.540 ₫

7.183.540 ₫

11.092.120 ₫ total

includes taxes & fees

25 Oct - 26 Oct

Cliffside Resort Condominiums

A spacious lobby with two sofas, a coffee table, and a flat-screen TV mounted on the wall.

A hotel room with a large bed, a bathroom with a bathtub, a TV on a wooden cabinet, and a chair.

A dining area with tables and chairs, a clock on the wall, and a counter with food items.

A hotel lobby with a reception desk, two sofas, a coffee table, and a carpeted floor.

13. 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, (1,001 reviews)

7.8/10

Good

(1,001 reviews)

"Enjoyed the stay, staff were friendly and pleasant the whole time, Breakfast was excellent!"

"Enjoyed the stay, staff were friendly and pleasant the whole time, Breakfast was excellent!"

United States

Michael

The price is 2.784.600 ₫

2.784.600 ₫

3.202.290 ₫ total

includes taxes & fees

4 Oct - 5 Oct

Quality Inn Old Saybrook - Westbrook

A waterfront property with a large house, multiple boats docked, and lush greenery.

A spacious lobby with multiple seating areas, a kitchen area, and large windows providing natural light.

A hotel lobby with a sofa, chairs, tables, and a large window.

A spacious hallway with a fireplace, a large window, and a built-in shelving unit.

14. Sag Harbor Inn

3.5 star property

10 km from The Heights

9.4 out of 10, Exceptional, (669 reviews)

9.4/10

Exceptional

(669 reviews)

"Free parking, clean, continental breakfast good quality."

"Free parking, clean, continental breakfast good quality."

United States

Terri

The price is 8.424.000 ₫

8.424.000 ₫

9.624.420 ₫ total

includes taxes & fees

4 Oct - 5 Oct

A spacious room with wicker furniture, large windows, and a view of the sea.

A beach scene with a wooden structure, two wooden chairs, a campfire, and string lights.

A coastal building with large windows, a deck, and a view of the sea at sunset.

A spacious room with large windows, a wooden bench, yoga mats, and a door leading to a balcony with a view of the sea.

15. Sound View Greenport

Sound View Greenport

4.0 star property

3.8 km from The Heights

8.4 out of 10, Very good, (737 reviews)

8.4/10

Very good

(737 reviews)

"Great one night stay."

"Great one night stay."

United States

Irene

The price is 6.506.500 ₫

6.506.500 ₫

8.176.237 ₫ total

includes taxes & fees

25 Oct - 26 Oct

Sound View Greenport

Two blue Adirondack chairs and a small white table in a grassy area surrounded by trees.

A guesthouse named Pier Blue with a sign, a parking lot, and a building with a red awning.

A hotel room with two beds, a wooden bench, a desk, a mirror, and a patterned carpet.

16. 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, (1,005 reviews)

8.0/10

Very good

(1,005 reviews)

"Nice room,"

"Nice room,"

United States

Russell

The price is 2.121.340 ₫

2.121.340 ₫

2.439.580 ₫ total

includes taxes & fees

29 Sept - 30 Sept

Pier Blue Inn Old Saybrook - Essex

A large hotel with a spacious outdoor patio area, multiple dining tables, and umbrellas.

A formal dining room with multiple tables and chairs, large windows with a city view, and a decorative carpet.

An aerial view of a coastal resort with a large pool, multiple buildings, and a well-maintained lawn.

A pool area with lounge chairs and umbrellas, a swimming pool, and a view of the sea.

17. 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, (1,009 reviews)

8.8/10

Excellent

(1,009 reviews)

"Wonderful"

"Wonderful"

United States

Bill

The price is 4.660.500 ₫

4.660.500 ₫

5.808.140 ₫ total

includes taxes & fees

7 Oct - 8 Oct

Water's Edge Resort & Spa

A living room with a stone fireplace, grey sofas, and a coffee table.

A bedroom with a large bed, a nightstand, a dresser, and a robe rack.

A modern lobby with a round gold table, a large framed floral painting, and a wooden desk.

A large, two-story house with a wrap-around porch, multiple windows, and a chimney.

18. The Captain Stannard

The Captain Stannard

3.0 star property

24 km from The Heights

9.8 out of 10, Exceptional, (283 reviews)

9.8/10

Exceptional

(283 reviews)

"Had a great stay. Everything was fantastic."

"Had a great stay. Everything was fantastic."

United States

Deborah

The price is 6.081.894 ₫

6.081.894 ₫

6.750.902 ₫ total

includes taxes & fees

28 Sept - 29 Sept

The Captain Stannard

A parking lot with a building in the background.

A motel with a large parking lot and multiple rooms.

A hotel room with two beds, a desk, a chair, a window with curtains, and two wall-mounted lamps.

A rectangular swimming pool with a fenced area, surrounded by trees and a concrete deck with white metal loungers.

19. Clinton Motel

2.5 star property

25.4 km from The Heights

8.6 out of 10, Excellent, (336 reviews)

8.6/10

Excellent

(336 reviews)

"Hotel was clean and the staff was pleasant. The pool was wonderful! I would stay there again."

"Hotel was clean and the staff was pleasant. The pool was wonderful! I would stay there again."

United States

Selena

The price is 2.054.000 ₫

2.054.000 ₫

2.362.100 ₫ total

includes taxes & fees

27 Sept - 28 Sept

A hotel room with a large bathtub, a desk with a lamp, a chair, and a bed with a red blanket.

A hotel lobby with a reception desk, a flat-screen TV mounted above a fireplace, and comfortable seating areas.

A multi-story residential building with blue trim and large windows.

A tranquil park with a gazebo, a pond with a fountain, and a building in the background.

20. Econo Lodge Inn & Suites Old Saybrook Westbrook

Econo Lodge Inn & Suites Old Saybrook Westbrook

2.0 star property

23.3 km from The Heights

7.2 out of 10, Good, (498 reviews)

7.2/10

Good

(498 reviews)

"It was a great place to stay Quiet and clean and staff was responsible"

"It was a great place to stay Quiet and clean and staff was responsible"

United States

Laurie

The price is 1.742.780 ₫

1.742.780 ₫

2.004.197 ₫ total

includes taxes & fees

25 Oct - 26 Oct

Econo Lodge Inn & Suites 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.

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

Where to stay in The Heights

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

Hay Beach

A calm lake with reflections of clouds, surrounded by trees and a distant structure.

View properties in map for Hay Beach

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

Ocean Vista Resort

Ocean Vista Resort

10/10 Excellent

"Staff was very friendly room was clean bed was comfortable"

Richard 1-night trip

Posted 6 hours ago

Ocean Vista Resort

Zey Hotel

Zey Hotel

10/10 Excellent

"Lovely hotel, great location and lovely courtyard!"

Martina 1-night trip

Posted 23 hours ago

Water's Edge Resort & Spa

Water's Edge Resort & Spa

8/10 Good

"The staff at the Bistro Bar weren't very good. Also the drinks sub par. I ordered a gin and tonic, they served me soda water twice."

Linda 3-night trip

Posted 1 day ago

Water's Edge Resort & Spa

The Shoals Suites and Slips

The Shoals Suites and Slips

10/10 Excellent

"This place is awesome! It is very well appointed and very comfortable beds. It's a beautiful space with lots of outdoor space and lovely views of the small marina next door. We were in town for just one night, wish we could have stayed longer. I'd go back in a heartbeat!"

Susan 1-night trip

Posted 2 days ago

The Shoals Suites and Slips

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

10/10 Excellent

"Beautiful and clean room and property with a gorgeous marina view. Friendly and helpful staff. I thoroughly enjoyed my stay, and intend to return."

Joseph 1-night trip

Posted 2 days ago

Saybrook Point Resort & Marina

Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows

10/10 Excellent

"Excellent stay. The room was clean and stylish. Can’t wait to come back"

Sarah 1-night trip

Posted 3 days ago

Silver Sands Motel & Beach Bungalows

The Bentley Hotel Southampton

The Bentley Hotel Southampton

10/10 Excellent

"I really appreciate the hotel. I will came back"

Elaine 1-night trip

Posted 5 days ago

The Bentley Hotel Southampton

Faraway Sag Harbor

Faraway Sag Harbor

10/10 Excellent

"Excellent hotel. Comfortable beds. Nice decorated. Very professional and friendly staff."

Miguel 2-night trip

Posted 11 days ago

Faraway Sag Harbor

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.

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.

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