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The Heights Hotels, Shelter Island Heights

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Our top choices for The Heights hotels

1. The Chequit

The Chequit
3.0 star property
The Heights
9.0 out of 10, Wonderful, (42 reviews)
"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 NZ$719
includes taxes & fees
9 Aug - 10 Aug
The Chequit

2. House on Chase Creek

House on Chase Creek
2.5 star property
The Heights
9.4 out of 10, Exceptional, (85 reviews)
"We had such an amazing stay! The house was beautiful, comfortable, and very clean. It is an easy walk to grab a great cup of coffee, which we loved. One of our favorite parts was sitting on the two Adirondack chairs on the water. The owner could not have been nicer and had great restaurant recommendations. We really loved it and will absolutely rebook soon!"
United States
Jeanine
The price is NZ$777
includes taxes & fees
3 Sept - 4 Sept
House on Chase Creek

3. Zey Hotel

Zey Hotel
3.5 star property
2.7 km from The Heights
9.2 out of 10, Wonderful, (366 reviews)
"Fantastic location and hugely helpful staff. I would absolutely stay again."
United States
Alex
The price is NZ$473
includes taxes & fees
18 Aug - 19 Aug
Zey Hotel

4. Shelter Island House

Shelter Island House
3.5 star property
0.9 km from The Heights
8.4 out of 10, Very good, (63 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."
United States
Dorothy
The price is NZ$615
includes taxes & fees
31 Aug - 1 Sept
Shelter Island House

5. West Neck Guesthouse

West Neck Guesthouse
3.5 star property
0.6 km from The Heights
8.2 out of 10, Very good, (43 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!"
United States
Allie
The price is NZ$609
includes taxes & fees
31 Aug - 1 Sept
West Neck Guesthouse

6. The Harbor Front Inn

The Harbor Front Inn
3.5 star property
2.4 km from The Heights
8.8 out of 10, Excellent, (634 reviews)
"Very nice property/staff and a great location"
United States
David
The price is NZ$801
includes taxes & fees
2 Sept - 3 Sept
The Harbor Front Inn

7. The Pridwin Hotel

The Pridwin Hotel
4.0 star property
2 km from The Heights
9.6 out of 10, Exceptional, (99 reviews)
"Stunning hotel! Will def stay again!"
United States
Anna
The price is NZ$1,392
includes taxes & fees
3 Sept - 4 Sept
The Pridwin Hotel

8. Sound View Greenport

Sound View Greenport
4.0 star property
3.8 km from The Heights
8.4 out of 10, Very good, (675 reviews)
"Great in town getaway"
United States
Yveline
The price is NZ$936
includes taxes & fees
27 Aug - 28 Aug
Sound View Greenport

9. 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, (311 reviews)
"Great stay"
United States
Connor
The price is NZ$735
includes taxes & fees
1 Sept - 2 Sept
The Shoals Suites and Slips

10. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
3.5 km from The Heights
9.0 out of 10, Wonderful, (279 reviews)
"Great place!"
United States
Christine
The price is NZ$1,024
includes taxes & fees
12 Aug - 13 Aug
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, (204 reviews)
"The hotel doesn’t reception doesn’t open till 9am. For early risers we had to leave the hotel just to get coffee. 9am is unheard of for a hotel"
United States
kerri
The price is NZ$824
includes taxes & fees
5 Aug - 6 Aug
American Beech Hotel

12. The Menhaden

The Menhaden
3.5 star property
2.4 km from The Heights
9.6 out of 10, Exceptional, (187 reviews)
"Staff was very accommodating and extremely nice, Great stay!"
United States
Lisa
The price is NZ$1,041
includes taxes & fees
5 Aug - 6 Aug
The Menhaden

13. Oyster Estate

Oyster Estate
2.0 star property
2.5 km from The Heights
9.2 out of 10, Wonderful, (284 reviews)
"Great location, great hotel, great staff! "
United States
Jenny
The price is NZ$1,022
includes taxes & fees
2 Sept - 3 Sept
Oyster Estate

14. North Fork Resort

North Fork Resort
3.0 star property
3.4 km from The Heights
9.4 out of 10, Exceptional, (44 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"
United States
Lisa
The price is NZ$1,219
includes taxes & fees
18 Aug - 19 Aug
North Fork Resort

15. Clinton Motel

Clinton Motel
2.5 star property
25.4 km from The Heights
8.6 out of 10, Excellent, (327 reviews)
"It was a nice motor lodge with chairs for sitting outside. There’s also a pool out back that was great."
United States
David
The price is NZ$164
includes taxes & fees
5 Aug - 6 Aug
Clinton Motel

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, (1,011 reviews)
"Cute place, clean and quiet."
United States
Wendy
The price is NZ$204
includes taxes & fees
25 Aug - 26 Aug
Pier Blue Inn Old Saybrook - Essex

17. 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, (485 reviews)
"Nice place , served it's purpose. Bed was very comfortable."
United States
Kenneth
The price is NZ$158
includes taxes & fees
19 Aug - 20 Aug
Econo Lodge Inn & Suites Old Saybrook Westbrook

18. Arbor View House B&B

Arbor View House B&B
3.5 star property
5.3 km from The Heights
9.4 out of 10, Exceptional, (16 reviews)
"Wonderful stay! Will definitely be back!"
United States
Lekecia
The price is NZ$1,221
includes taxes & fees
3 Sept - 4 Sept
Arbor View House B&B

19. Sag Harbor Inn

Sag Harbor Inn
3.5 star property
10 km from The Heights
9.4 out of 10, Exceptional, (653 reviews)
"Everything about the place was great - great value overlooking the Harbor!"
United States
Christopher
The price is NZ$989
includes taxes & fees
20 Aug - 21 Aug
Sag Harbor Inn

20. 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, (1,003 reviews)
"Very friendly staff, easy parking, great breakfast, and clean towels and beds made daily. Great place to stay."
United States
John
The price is NZ$198
includes taxes & fees
2 Sept - 3 Sept
Quality Inn 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.

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 program—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.

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