The Heights Hotels, Shelter Island Heights

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4012 Cheap Hotels in The Heights - Specials, Reviews, & Last Minute Deals

House on Chase Creek

2.5 star property
9.4 out of 10, Exceptional, (76)
"The House on Chase Creek is beautiful. It's an old house but everything is updated, clean and comfortable. "
The price is NZ$418
includes taxes & fees
6 Oct - 7 Oct
House on Chase Creek

The Chequit

3.0 star property
9.0 out of 10, Wonderful, (36)
"Everyone was amazing "
The Chequit

The 1770 House Restaurant & Inn

4.0 star property
9.8 out of 10, Exceptional, (157)
"The staff was incredibly genuine and the property felt intimate and comfortable."
The price is NZ$755
includes taxes & fees
6 Oct - 7 Oct
The 1770 House Restaurant & Inn

Silver Sands Motel & Beach Bungalows

4.0 star property
9.8 out of 10, Exceptional, (126)
"We had a great time, it’s a beautiful property and there’s plenty to do downtown. It was our first time here and we’ll definitely be back. "
Silver Sands Motel & Beach Bungalows

Westbrook Inn B&B

3.0 star property
9.8 out of 10, Exceptional, (166)
"Beautiful place and wonderful staff"
The price is NZ$419
includes taxes & fees
23 Sept - 24 Sept
Westbrook Inn B&B

Canoe Place Inn and Cottages

4.0 star property
9.8 out of 10, Exceptional, (56)
"Amazing property. Really enjoyed our stay."
Canoe Place Inn and Cottages

The Roundtree, Amagansett

4.5 star property
9.8 out of 10, Exceptional, (89)
"The Roundtree was one of the most peaceful hotels we’ve ever stayed in. I highly recommend for a romantic getaway. "
The price is NZ$1,213
includes taxes & fees
1 Oct - 2 Oct
The Roundtree, Amagansett

The Pridwin Hotel

4.0 star property
9.6 out of 10, Exceptional, (77)
"Shelter Island is definitely a gem"
The Pridwin Hotel

The Shoals Suites and Slips

3.5 star property
9.6 out of 10, Exceptional, (206)
"Loved our stay"
The price is NZ$485
includes taxes & fees
22 Sept - 23 Sept
The Shoals Suites and Slips

The Captain Stannard

3.0 star property
9.6 out of 10, Exceptional, (247)
"Everything was fantastic, will stay again!"
The Captain Stannard

The Menhaden

3.5 star property
9.6 out of 10, Exceptional, (162)
"Great little boutique hotel. Staff were very helpful and accommodating. Great restaurants and wineries in the area. Would highly recommend!"
The price is NZ$804
includes taxes & fees
8 Oct - 9 Oct
The Menhaden

The Hedges Inn

3.5 star property
9.6 out of 10, Exceptional, (71)
"Great staff "
The price is NZ$1,130
includes taxes & fees
21 Sept - 22 Sept
The Hedges Inn

East Hampton Art House Bed & Breakfast

4.0 star property
9.6 out of 10, Exceptional, (64)
"Roz and Michael built a beautiful paradise that they enjoy sharing with you. Everything is amazing. "
The price is NZ$1,108
includes taxes & fees
29 Sept - 30 Sept
East Hampton Art House Bed & Breakfast

The Bentley Hotel Southampton

2.0 star property
9.6 out of 10, Exceptional, (338)
"Return visitor. Great stay."
The price is NZ$392
includes taxes & fees
29 Sept - 30 Sept
The Bentley Hotel Southampton

James Pharmacy Bed & Breakfast

4.0 star property
9.4 out of 10, Exceptional, (18)
"My husband and I stayed here for a quick weekend getaway and loved our experience! The location was perfect - located near restaurants, shops, and the beach - and the room was clean and charming. We will definitely be back!"
The price is NZ$513
includes taxes & fees
1 Oct - 2 Oct
James Pharmacy Bed & Breakfast

Madison Beach Hotel

4.0 star property
9.4 out of 10, Exceptional, (318)
"the staff was exceptional and our dinner was very good"
The price is NZ$713
includes taxes & fees
29 Sept - 30 Sept
Madison Beach Hotel

Bridgehampton Inn

3.5 star property
9.4 out of 10, Exceptional, (216)
"Lovely inn, with very accommodating staff. "
The price is NZ$581
includes taxes & fees
6 Oct - 7 Oct
Bridgehampton Inn

Sag Harbor Inn

3.5 star property
9.4 out of 10, Exceptional, (553)
"Great place to stay!"
The price is NZ$549
includes taxes & fees
6 Oct - 7 Oct
Sag Harbor Inn

Saybrook Point Resort & Marina

3.5 star property
9.4 out of 10, Exceptional, (1005)
"Very pleasant property with friendly staff in all areas we experienced. We had a very good stay and can recommend the property. "
The price is NZ$736
includes taxes & fees
13 Oct - 14 Oct
Saybrook Point Resort & Marina

Greenporter Hotel

2.0 star property
9.4 out of 10, Exceptional, (232)
"Staff was amazing and this hotel is in the perfect location "
Greenporter Hotel
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

Find out more about 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.

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Explore a world of travel with Expedia

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.

Where is the best place to stay in The Heights?

Based on Expedia customer reviews, The Chequit is the highest ranked property in The Heights. This hotel offers a restaurant and free parking. Another top choice in the area is House on Chase Creek.

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 14 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.