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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
9.2 out of 10, Wonderful, (59 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$413
includes taxes & fees
4 Oct - 5 Oct
The Chequit

2. House on Chase Creek

House on Chase Creek
2.5 star property
The Heights
9.4 out of 10, Exceptional, (86 reviews)
"Nice owner.. convenient location"
United States
Calvin
The price is NZ$429
includes taxes & fees
5 Oct - 6 Oct
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, (405 reviews)
"Great location…thoroughly enjoyed our time."
United States
Renee
The price is NZ$336
includes taxes & fees
27 Sept - 28 Sept
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, (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."
United States
Dorothy
The price is NZ$401
includes taxes & fees
4 Oct - 5 Oct
Shelter Island House

5. The Harbor Front Inn

The Harbor Front Inn
3.5 star property
2.4 km from The Heights
9.0 out of 10, Wonderful, (655 reviews)
"Great location"
United States
Jordan
The price is NZ$522
includes taxes & fees
12 Oct - 13 Oct
The Harbor Front Inn

6. 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, (169 reviews)
"I love this place"
United States
Sirikhwan
The price is NZ$557
includes taxes & fees
19 Oct - 20 Oct
Silver Sands Motel & Beach Bungalows

7. Sound View Greenport

Sound View Greenport
4.0 star property
3.8 km from The Heights
8.4 out of 10, Very good, (730 reviews)
"Great one night stay."
United States
Irene
The price is NZ$537
includes taxes & fees
1 Oct - 2 Oct
Sound View Greenport

8. 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)
"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$625
includes taxes & fees
1 Oct - 2 Oct
West Neck Guesthouse

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, (340 reviews)
"Loved everything about our stay!"
United States
Melissa
The price is NZ$446
includes taxes & fees
1 Oct - 2 Oct
The Shoals Suites and Slips

10. American Beech Hotel

American Beech Hotel
3.5 star property
2.6 km from The Heights
9.0 out of 10, Wonderful, (207 reviews)
"Great location, very friendly and helpful "
United States
Mary
The price is NZ$546
includes taxes & fees
21 Sept - 22 Sept
American Beech Hotel

11. Oyster Estate

Oyster Estate
4.0 star property
2.5 km from The Heights
9.2 out of 10, Wonderful, (288 reviews)
"Honestly I was blown away by the hospitality and cleanliness of the new updated hotel. Recommend to all."
United States
Matthew
The price is NZ$688
includes taxes & fees
30 Sept - 1 Oct
Oyster Estate

12. The Menhaden

The Menhaden
3.5 star property
2.4 km from The Heights
9.6 out of 10, Exceptional, (191 reviews)
"Staff was very accommodating and extremely nice, Great stay!"
United States
Lisa
The price is NZ$805
includes taxes & fees
7 Oct - 8 Oct
The Menhaden

13. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
3.5 km from The Heights
9.0 out of 10, Wonderful, (292 reviews)
"Great place!"
United States
Christine
The price is NZ$742
includes taxes & fees
5 Oct - 6 Oct
Cliffside Resort Condominiums

14. North Fork Resort

North Fork Resort
3.0 star property
3.4 km from The Heights
9.6 out of 10, Exceptional, (56 reviews)
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
United States
Harold
The price is NZ$558
includes taxes & fees
18 Oct - 19 Oct
North Fork Resort

15. The Pridwin Hotel

The Pridwin Hotel
4.0 star property
2 km from The Heights
9.4 out of 10, Exceptional, (120 reviews)
"We had a great weekend here. A bit pricy but 100% worth the money"
United States
Morris
The price is NZ$3,183
includes taxes & fees
19 Sept - 20 Sept
The Pridwin Hotel

16. Sag Harbor Inn

Sag Harbor Inn
3.5 star property
10 km from The Heights
9.4 out of 10, Exceptional, (665 reviews)
"Location and scenery"
United States
Loretta
The price is NZ$646
includes taxes & fees
4 Oct - 5 Oct
Sag Harbor Inn

17. Faraway Sag Harbor

Faraway Sag Harbor
4.0 star property
10.1 km from The Heights
9.0 out of 10, Wonderful, (308 reviews)
"Excellent hotel. Comfortable beds. Nice decorated. Very professional and friendly staff."
United States
Miguel
The price is NZ$977
includes taxes & fees
4 Oct - 5 Oct
Faraway Sag Harbor

18. 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, (1,003 reviews)
"Pleasant one night stay in our trek"
United States
Carolyn
The price is NZ$164
includes taxes & fees
23 Sept - 24 Sept
Pier Blue Inn Old Saybrook - Essex

19. Clinton Motel

Clinton Motel
2.5 star property
25.4 km from The Heights
8.6 out of 10, Excellent, (336 reviews)
"Hotel was clean and the staff was pleasant. The pool was wonderful! I would stay there again."
United States
Selena
The price is NZ$159
includes taxes & fees
21 Sept - 22 Sept
Clinton Motel

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, (1,001 reviews)
"Enjoyed the stay, staff were friendly and pleasant the whole time, Breakfast was excellent!"
United States
Michael
The price is NZ$203
includes taxes & fees
12 Oct - 13 Oct
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 Greenport Carousel and Greenport Harbor Brewing Company, 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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