Lodging Image

The Heights Hotels, Shelter Island Heights

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Filter by

Property class

Guest rating

Selecting then applying a filter from this group will update the results on a new page

Our top choices for The Heights hotels

1. The Chequit

The Chequit
3.0 star property
The Heights
9.0 out of 10, Wonderful, (75 reviews)
"Friendly staff , Unique property."
United States
Patrick
The price is NZ$338
includes taxes & fees
25 Nov - 26 Nov
The Chequit

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 NZ$375
includes taxes & fees
9 Nov - 10 Nov
House on Chase Creek

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, (674 reviews)
"Such a lovely place for a getaway. Charming town and lovely water views!"
United States
Laura
The price is NZ$318
includes taxes & fees
17 Nov - 18 Nov
The Harbor Front Inn

4. Zey Hotel

Zey Hotel
3.5 star property
2.7 km from The Heights
9.2 out of 10, Wonderful, (441 reviews)
"Great location…thoroughly enjoyed our time."
United States
Renee
The price is NZ$273
includes taxes & fees
4 Nov - 5 Nov
Zey Hotel

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, (187 reviews)
"Nicely renovated and enjoyable."
United States
Becky
The price is NZ$441
includes taxes & fees
2 Dec - 3 Dec
Silver Sands Motel & Beach Bungalows

6. Oyster Estate

Oyster Estate
4.0 star property
2.5 km from The Heights
9.2 out of 10, Wonderful, (301 reviews)
"incredible stay, pet friendly and very accommodating. Staff was so kind!"
United States
Allison
The price is NZ$439
includes taxes & fees
3 Nov - 4 Nov
Oyster Estate

7. Sound View Greenport

Sound View Greenport
4.0 star property
3.8 km from The Heights
8.4 out of 10, Very good, (763 reviews)
"The ambience is amazing! We loved our stay!!"
United States
Christine
The price is NZ$360
includes taxes & fees
16 Nov - 17 Nov
Sound View Greenport

8. 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, (349 reviews)
"Very clean property, beautiful view, and quiet."
United States
Masayo
The price is NZ$379
includes taxes & fees
10 Nov - 11 Nov
The Shoals Suites and Slips

9. The Menhaden

The Menhaden
3.5 star property
2.4 km from The Heights
9.6 out of 10, Exceptional, (195 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 NZ$631
includes taxes & fees
1 Dec - 2 Dec
The Menhaden

10. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
3.5 km from The Heights
9.0 out of 10, Wonderful, (299 reviews)
"Great condo. Very nice location and grounds."
United States
William
The price is NZ$540
includes taxes & fees
12 Nov - 13 Nov
Cliffside Resort Condominiums

11. 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 NZ$580
includes taxes & fees
3 Nov - 4 Nov
American Beech Hotel

12. North Fork Resort

North Fork Resort
3.0 star property
3.4 km from The Heights
9.6 out of 10, Exceptional, (72 reviews)
"Everything was perfect 💞"
United States
Altynai
The price is NZ$637
includes taxes & fees
3 Nov - 4 Nov
North Fork Resort

13. Sag Harbor Inn

Sag Harbor Inn
3.5 star property
10 km from The Heights
9.4 out of 10, Exceptional, (684 reviews)
"The room was nicely appointed; sufficient parking; close to downtown; and a nice variety for breakfast."
United States
Annie
The price is NZ$444
includes taxes & fees
3 Nov - 4 Nov
Sag Harbor Inn

14. Faraway Sag Harbor

Faraway Sag Harbor
4.0 star property
10.1 km from The Heights
9.0 out of 10, Wonderful, (320 reviews)
"Great location , wonderful lobby bar Cute rooms"
United States
Thomas
The price is NZ$713
includes taxes & fees
16 Nov - 17 Nov
Faraway Sag Harbor

15. The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
22.6 km from The Heights
9.6 out of 10, Exceptional, (615 reviews)
"great spot to stay,"
United States
Armando
The price is NZ$335
includes taxes & fees
3 Nov - 4 Nov
The Bentley Hotel Southampton

16. The Atlantic Hotel

The Atlantic Hotel
2.5 star property
22.1 km from The Heights
7.2 out of 10, Good, (1,003 reviews)
"Lots of parking, rooms were clean and smelt nice"
United States
miranda
The price is NZ$254
includes taxes & fees
24 Nov - 25 Nov
The Atlantic Hotel

17. Shorewood Inn

Shorewood Inn
2.5 star property
24.5 km from The Heights
8.4 out of 10, Very good, (843 reviews)
"Beautiful hotel vintage"
United States
Dennis
The price is NZ$252
includes taxes & fees
3 Nov - 4 Nov
Shorewood Inn

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, (351 reviews)
"the place is great. the location was excellent for the film festival. The room itself was very roomy clean cute little balcony. I will book it again for the festival."
United States
Tina
The price is NZ$342
includes taxes & fees
3 Nov - 4 Nov
East Hampton House Resort

19. Hamlet Inn

Hamlet Inn
2.0 star property
23.1 km from The Heights
8.6 out of 10, Excellent, (518 reviews)
"You can't find a nicer owner, or a more laid back conveniently located spot"
United States
Eric
The price is NZ$246
includes taxes & fees
3 Nov - 4 Nov
Hamlet Inn

20. 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, (1,009 reviews)
"Staff was friendly. Grounds very well kept. But rooms are very dated."
United States
Kevin
The price is NZ$167
includes taxes & fees
9 Nov - 10 Nov
Pier Blue Inn Old Saybrook - Essex
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.

Compare popular hotels in The Heights

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet-friendly
WiFi included
A large, multi-story building with a porch and outdoor seating area, featuring multiple windows and a balcony.
The Chequit
3.0 star property
9.0
Wonderful
75 reviews
View
A serene landscape with a calm body of water reflecting trees with autumn foliage.
House on Chase Creek
2.5 star property
9.4
Exceptional
87 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
674 reviews
View
A two-story house with a balcony, outdoor seating area, and a variety of plants.
Zey Hotel
3.5 star property
9.2
Wonderful
441 reviews
View
A beachside outdoor seating area with white Adirondack chairs and a fire pit.
Silver Sands Motel & Beach Bungalows
4.0 star property
10.0
Exceptional
187 reviews
View

Our guide on where to stay in The Heights

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

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

Recent Reviews in The Heights

Find out more about The Heights

Top reasons to visit The Heights

  • Stunning Beaches: The Heights boasts beautiful beaches with crystal-clear waters, perfect for swimming and sunbathing.
  • Outdoor Activities: Enjoy a range of sports, including golfing and relaxing at private clubs amidst scenic landscapes.
  • Rich Cultural Experience: Explore historic buildings and vibrant local culture, making it ideal for families.
  • Scenic Parks: Relax in lush parks, perfect for picnics and leisurely strolls with stunning mountain views.
  • Diverse Accommodation: Choose from spacious hotels and agritourism options, many featuring pet-friendly amenities.

Find great hotels near The Heights

Discover a variety of accommodation options in The Heights, Shelter Island Heights, where you can find spacious hotels and agritourism properties. Ideal for families and adventurers alike, many establishments offer pet-friendly amenities to ensure a comfortable stay. Whether you're seeking a relaxing getaway or a fun-filled family holiday, The Heights has something to cater to your every need, making it the perfect destination for your next vacation.

  • Sound View Greenport: Nestled 3.2km from The Heights, Sound View Greenport combines a family-friendly atmosphere with essential business amenities. This 3.5-star hotel is ideal for those travelling with children, offering safety features like window guards and complimentary cribs. Business travellers will appreciate the dedicated meeting rooms and conference space, ensuring a productive stay. Additionally, the hotel welcomes pets, allowing you to bring your furry friends along for the adventure.
  • Sag Harbor Inn: Located 9.7km from The Heights, Sag Harbor Inn is a charming 3.5-star accommodation tailored for business-minded guests. With a focus on providing a comfortable yet professional environment, the inn features meeting rooms equipped to cater to corporate needs. Its serene setting makes it a perfect retreat after a day of meetings, offering a peaceful ambiance for relaxation and reflection in the picturesque surroundings of Sag Harbor.
  • The Harbor Front Inn: Just 1.6km from The Heights, The Harbor Front Inn is a delightful choice for travellers seeking both business facilities and pet-friendly accommodations. This 3.5-star hotel boasts a welcoming environment for pets, allowing dogs to stay in your room while you enjoy the nearby attractions. With its focus on business services, including meeting facilities, the inn caters to those wanting a productive stay while also providing the comforts of home, making it an excellent choice for both work and leisure.

Where to stay near The Heights

For an unforgettable vacation in The Heights, indulge in outdoor sports and family-friendly activities amidst stunning mountain views. Enjoy easy access to lush parks and recreational spaces perfect for picnics and leisurely strolls. Nearby, explore the charming Shelter Island, rich in history and scenic beauty, ideal for excursions. Whether it's luxury stays or captivating landscapes, The Heights promises a delightful blend of adventure and relaxation for every traveller.

  • Hamptons: A mere 16.1km from The Heights, the Hamptons is famed for its stunning beaches and vibrant outdoor activities. This area draws visitors primarily in the summer months, offering a romantic atmosphere perfect for couples looking to unwind. Enjoy activities like golfing, attending music concerts, or relaxing at luxury resorts. The local beaches and tranquil lakes provide the ideal backdrop for a leisurely day in the sun, making it a must-visit for beach lovers.
  • Greenport: Located just 3.2km away, Greenport is a charming city that captures the essence of seaside living. With a similar seasonal visitor pattern, summer brings a buzz of outdoor and romantic activities. You can immerse yourself in the local culture by exploring its golf courses, enjoying live music, or attending events at the conference venues. The nearby beaches and family-friendly areas make Greenport a perfect spot for those seeking relaxation and leisure in a picturesque coastal setting.
  • Sag Harbor: Only 11.3km from The Heights, Sag Harbor is renowned for its historic charm and stunning waterfront views. Visitors flock here during the summer for a rich outdoor experience, with opportunities for beach outings and romantic strolls along the shore. Engage in thrilling activities like skiing in nearby fields or simply enjoy the scenic parks and family-friendly beaches that dot the area. Sag Harbor offers a delightful blend of relaxation and adventure, making it an attractive destination for travellers.

Things to do near The Heights

The Heights in Shelter Island Heights offers a fantastic blend of sports and outdoor activities, perfect for an entertaining holiday. You can enjoy golfing at the local golf course or relax at a country private club. With vibrant outdoor entertaining areas, it's an ideal spot for making the most of your time in this charming destination.

Shopping

The Heights offers a delightful shopping experience with local charm. Visit the Greenport Farmers' Market, 3.2km away, for fresh produce and artisanal goods. The Style Bar, 9.7km from The Heights, boasts trendy fashion, while Love Lane, 17.7km away, is perfect for family-friendly shopping.

Recreation

Shelter Island Whale's Tail offers a fun-filled mini golf experience just 1.6km from The Heights, perfect for families and adventure seekers. For a more tranquil outing, Cedar Point County Park, 11.3km away, provides a peaceful environment for relaxation and wellness amidst nature.

Adventure

Splish Splash Water Park, located 35.4km from The Heights, offers exhilarating water slides and family-friendly attractions. For hiking enthusiasts, the Walking Dunes Trailhead, 27.4km away, presents breathtaking scenery and outdoor adventure. Experience high-speed thrills at Riverhead Raceway, situated 33.8km from The Heights, perfect for motorsport fans.

Nightlife

The Heights offers a delightful nightlife with the Greenport Carousel, just 1.6km away, perfect for outdoor fun. For culture and romance, visit the Bay Street Theatre, six miles from The Heights. If movies are your thing, the Regal UA East Hampton cinema, 19.3km away, is a must-visit.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for The Heights

To save money on your trip to The Heights, consider visiting between January and March when hotel prices are at their lowest. Book your stay on a Tuesday for better rates, while avoiding Saturdays, which are the priciest. Use Expedia to filter accommodation options based on your budget and preferences, and look for package deals that combine flights, hotels, and activities for added savings. Additionally, take advantage of free local attractions and consider walking or using affordable public transport to explore the area without breaking the bank.

  • The most and least expensive months on average to stay in a hotel: The hotel pricing around The Heights is moderately seasonal. The cheapest months to stay around The Heights are January to March, where the prices are moderately lower. This is in comparison to June to August, where prices are moderately higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay around The Heights is Tuesday. The most expensive day to stay around The Heights is Saturday.
  • Find cheap hotels on Expedia: Utilise Expedia’s search tool to refine your preferences, such as your budget, desired location, and the type of accommodation you’re looking for. To find the best prices and deals, simply arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can save a bit of cash by combining your stay at The Heights hotel with your flights and activities through an Expedia package deal.

Find the best attractions near The Heights

The Heights in Shelter Island Heights, New York, is perfect for a sports and outdoor-themed getaway. Visitors can enjoy stunning beaches, explore historic buildings, and relax in urban parks. The area offers a rich cultural experience suitable for families, with plenty of attractions nearby, including living areas and scenic spots like Table Hill. Whether you're after adventure or leisure, The Heights has something for everyone.

  • 67 Steps Beach: A picturesque beach perfect for soaking up the sun and enjoying the refreshing ocean breeze. With its unique 67 steps leading down to the sand, this beach offers a relaxing atmosphere just 4.8km from The Heights, ideal for swimming and beachcombing.
  • Railroad Museum of Long Island: Located only 1.6km away, this museum showcases the rich history of railroads in Long Island. With engaging exhibits and vintage trains, it offers a cultural experience that transports you through time.
  • Orient Point County Park: Situated 12.9km from The Heights, this urban park is perfect for families seeking outdoor adventures. Enjoy scenic walking trails, picnic areas, and stunning views of the Long Island Sound, making it a delightful day out.

Best time to go to The Heights

The best time to visit The Heights can depend on the weather and when visitor numbers rise and fall. The hottest average temperature around The Heights falls in August, when visitor numbers are moderately high and weather is mostly sunny with light rain. The coolest average temperature around The Heights falls in January, visitor numbers are moderately low and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January35.6°F (2.0°C)Light RainMostly SunnyModerately LowModerately Low
February35.8°F (2.1°C)Light RainMostly CloudyModerately LowModerately Low
March39.7°F (4.3°C)Light RainMostly SunnyAverageModerately Low
April47.5°F (8.6°C)Light RainMostly SunnyAverageAverage
May55.8°F (13.2°C)Light RainMostly SunnyAverageAverage
June64.9°F (18.3°C)Light RainMostly SunnyModerately HighModerately High
July73.0°F (22.8°C)Light RainMostly SunnyModerately HighModerately High
August73.4°F (23.0°C)Light RainMostly SunnyModerately HighModerately High
September68.2°F (20.1°C)Light RainMostly SunnyAverageAverage
October59.7°F (15.4°C)Light RainMostly SunnyAverageAverage
November49.6°F (9.8°C)Light RainMostly SunnyAverageAverage
December42.1°F (5.6°C)Light RainMostly CloudyModerately LowAverage

The nearest major airports for your trip to The Heights

To reach The Heights on Shelter Island, you'll find several major airports nearby. Islip, NY (ISP-MacArthur) is situated 70.8km away, with hotel options like the 3.5-star Hyatt Regency Long Island and Jake's 58 Casino Hotel, both 6.4km from the airport. New Haven, CT (HVN-Tweed) is 49.9km away, featuring hotels such as The Blake Hotel and Graduate by Hilton, both 4.8km from the airport. East Hampton, NY (HTO) is the closest at 16.1km, with luxurious stays like the 5-star Mill House Inn and the 4.5-star Topping Rose House, both just 4.8km from the airport.

Frequently asked questions

When is the best time to go to The Heights?
The best times to go to The Heights are during the spring (April to June) and autumn (September to November) months.

During these periods, the weather is generally pleasant, with comfortable temperatures and less humidity than the summer. This makes it ideal for exploring the neighbourhood's parks and outdoor attractions, such as the walking paths along the Hudson River and the smaller, well-kept community gardens. You'll find the trees in full bloom in spring or showcasing beautiful colours in autumn, which adds to the area's appeal.

Couples often appreciate the romantic feel of The Heights during these seasons, as the milder weather is great for leisurely strolls, dining outdoors, and enjoying the scenic views of the Manhattan skyline without the intense heat or cold. Many local cafes and restaurants offer outdoor seating, allowing you to soak in the local atmosphere.

For solo travellers, these seasons provide an excellent opportunity to explore at your own pace. The quieter periods between major tourist rushes mean you can enjoy local shops, galleries, and museums without large crowds.
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 to 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 hotel booking in The Heights with Expedia?
One Key™—Expedia's free travel rewards programme—gives you instant access to discounts with Member Prices on The Heights hotels. Plus, you'll earn OneKeyCash™* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings. *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
How much is the nightly rate for a hotel in The Heights?
Hotel prices in The Heights often vary, but you can find a great deal 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.

Explore a world of travel with Expedia