A pebbled beach with a sunset and a distant bridge.

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Our top choices for Shelter Island Heights hotels

1. The Pridwin Hotel

The Pridwin Hotel
4.0 star property
Shelter Island Heights
9.6 out of 10, Exceptional, (95 reviews)
"Stunning hotel! Will def stay again!"
United States
Anna
The price is ąøæ21,809
ąøæ27,409 total
includes taxes & fees
25 Aug - 26 Aug
The Pridwin Hotel

2. 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 ąøæ12,888
ąøæ14,724 total
includes taxes & fees
28 Jul - 29 Jul
The Chequit

3. Shelter Island House

Shelter Island House
3.5 star property
Shelter Island Heights
8.4 out of 10, Very good, (61 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 ąøæ10,656
ąøæ12,174 total
includes taxes & fees
13 Aug - 14 Aug
Shelter Island House

4. West Neck Guesthouse

West Neck Guesthouse
3.5 star property
Shelter Island Heights
8.2 out of 10, Very good, (42 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 ąøæ10,563
ąøæ12,069 total
includes taxes & fees
27 Jul - 28 Jul
West Neck Guesthouse

5. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
Greenport
9.8 out of 10, Exceptional, (160 reviews)
"Amazing!"
United States
Joseph
Silver Sands Motel & Beach Bungalows

6. The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
8.8 out of 10, Excellent, (632 reviews)
"Very nice property/staff and a great location"
United States
David
The price is ąøæ13,162
ąøæ16,770 total
includes taxes & fees
19 Aug - 20 Aug
The Harbor Front Inn

7. Zey Hotel

Zey Hotel
3.5 star property
Greenport
9.2 out of 10, Wonderful, (361 reviews)
"Great atmosphere, lovely hotel! We had a great time."
United States
Luis
The price is ąøæ8,188
ąøæ9,354 total
includes taxes & fees
25 Aug - 26 Aug
Zey Hotel

8. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (275 reviews)
"Comfortable and clean, and the beach location is amazing. The sunset was spectacular. We will definitely come back again!"
United States
Suzanne
The price is ąøæ9,438
ąøæ12,248 total
includes taxes & fees
29 Jul - 30 Jul
Cliffside Resort Condominiums

9. The Menhaden

The Menhaden
3.5 star property
Greenport
9.6 out of 10, Exceptional, (185 reviews)
"Staff was very accommodating and extremely nice, Great stay!"
United States
Lisa
The price is ąøæ18,650
ąøæ22,656 total
includes taxes & fees
27 Jul - 28 Jul
The Menhaden

10. The Shoals Suites and Slips

The Shoals Suites and Slips
3.5 star property
Southold
9.4 out of 10, Exceptional, (303 reviews)
"It is a beautiful upscale property. The rooms are very comfortable & had all the amenities you needed. Very good location making it accessible for anything you wanted to do in the area."
United States
Sue
The price is ąøæ12,527
ąøæ15,155 total
includes taxes & fees
27 Jul - 28 Jul
The Shoals Suites and Slips

11. American Beech Hotel

American Beech Hotel
3.5 star property
Greenport
9.0 out of 10, Wonderful, (203 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 ąøæ15,802
ąøæ19,402 total
includes taxes & fees
27 Jul - 28 Jul
American Beech Hotel

12. Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very good, (667 reviews)
"Location was the best. Enjoyed using the pool. View from the room of the Long Island sound was incredible. We had dinner at Haylard restaurant. On the premises and it was delicious."
United States
rosemary
The price is ąøæ11,390
ąøæ15,900 total
includes taxes & fees
19 Aug - 20 Aug
Sound View Greenport

13. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.4 out of 10, Exceptional, (37 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"
United States
Lisa
The price is ąøæ19,778
ąøæ22,597 total
includes taxes & fees
10 Aug - 11 Aug
North Fork Resort

14. Sag Harbor Inn

Sag Harbor Inn
3.5 star property
Sag Harbor
9.4 out of 10, Exceptional, (650 reviews)
"Everything about the place was great - great value overlooking the Harbor!"
United States
Christopher
The price is ąøæ17,150
ąøæ19,594 total
includes taxes & fees
9 Aug - 10 Aug
Sag Harbor Inn

15. Faraway Sag Harbor

Faraway Sag Harbor
4.0 star property
Sag Harbor
9.0 out of 10, Wonderful, (297 reviews)
"Great location in the heart of town Walk to everything Amazing breakfast too "
United States
Michael
The price is ąøæ32,515
ąøæ40,863 total
includes taxes & fees
27 Jul - 28 Jul
Faraway Sag Harbor

16. Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
Old Saybrook
7.8 out of 10, Good, (1,009 reviews)
"The ease of checking in - the breakfast was a nice addition to have included in the price of the inn. Breakfast was very nice with lots of choices to choose from"
United States
Janice
The price is ąøæ3,981
ąøæ4,578 total
includes taxes & fees
23 Aug - 24 Aug
Quality Inn Old Saybrook - Westbrook

17. Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (325 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 ąøæ3,100
ąøæ3,565 total
includes taxes & fees
27 Jul - 28 Jul
Clinton Motel

18. Saybrook Point Resort & Marina

Saybrook Point Resort & Marina
3.5 star property
Old Saybrook Center
9.6 out of 10, Exceptional, (1,015 reviews)
"Beautiful resort!! Great location! Rooms were spacious, comfortable and very clean! Restaurant a must do!"
United States
Marilyn
The price is ąøæ13,781
ąøæ17,027 total
includes taxes & fees
5 Aug - 6 Aug
Saybrook Point Resort & Marina

19. The Captain Stannard

The Captain Stannard
3.0 star property
Westbrook Center
9.6 out of 10, Exceptional, (270 reviews)
"Loved the beautiful porch and closeness to beach. The bed and linens were so comfortable."
United States
Judith
The price is ąøæ7,882
ąøæ8,749 total
includes taxes & fees
9 Aug - 10 Aug
The Captain Stannard

20. Water's Edge Resort & Spa

Water's Edge Resort & Spa
3.5 star property
Westbrook Center
8.8 out of 10, Excellent, (1,005 reviews)
"Very nice place would stay again."
United States
Cary
The price is ąøæ10,075
ąøæ12,167 total
includes taxes & fees
26 Aug - 27 Aug
Water's Edge Resort & Spa
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Where to stay in Shelter Island Heights

Find the best Shelter Island Heights areas for the activities you enjoy most.

The Heights

If you're spending some time in The Heights, Sunset Beach and Shelter Island Country Club are top sights worth seeing.

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.

Stay near popular Shelter Island Heights attractions

Learn more about Shelter Island Heights

Victorian homes line the streets of this charming hamlet where you can rent bikes to explore the island's quiet beaches. Reserve a table at one of the waterfront restaurants for sunset views or take the short ferry to Greenport for more dining options.

A marina with numerous sailboats docked, a large tree in the foreground, and a flagpole with an American flag.
Photo by Brian V. Rowe
Open Photo by Brian V. Rowe

Top Shelter Island Heights Hotel Reviews

More cheap stays in Shelter Island Heights

Find out more about Shelter Island Heights

Top reasons to visit Shelter Island Heights

  • Scenic Outdoor Activities: Enjoy a variety of outdoor adventures, from golfing to leisurely bike rides along picturesque routes.
  • Charming Beaches: Relax on beautiful beaches that offer tranquil waterfront views and opportunities for water sports.
  • Family-Friendly Attractions: Explore a range of attractions suitable for families, ensuring fun for all ages.
  • Quaint Neighbourhoods: Stroll through charming streets filled with historic buildings and local culture.
  • Diverse Accommodation: Choose from cosy bed and breakfasts to unique agritourism properties that cater to every traveller's needs.

Find great hotels near Shelter Island Heights

Experience the charm of Shelter Island Heights, where a variety of accommodation options await, including cosy bed and breakfasts and unique agritourism properties. This idyllic destination caters to families, adventure seekers, and pet-friendly travellers alike, ensuring a memorable getaway. Whether you’re looking for the perfect Shelter Island House or a welcoming hotel, you’ll find numerous properties that offer both comfort and convenience amid the scenic beauty of this serene locale.

  • Sound View Greenport: Nestled merely 3km from Shelter Island Heights, Sound View Greenport is a 3.5-star hotel that exudes a relaxed beachside charm. With a guest rating of 8.4 out of 10, it is an excellent choice for families and pet lovers alike. The property boasts direct access to the beach, allowing guests to indulge in sun-soaked days by the sea. Amenities for children, including free cribs and window guards, ensure a family-friendly environment. Additionally, the hotel accommodates pets with a welcoming policy that permits dogs and cats, making it a delightful option for those travelling with furry companions.
  • Sag Harbor Inn: Located 10km from Shelter Island Heights, Sag Harbor Inn is a distinguished 3.5-star establishment with an exceptional guest rating of 9.4 out of 10. This inn caters primarily to business travellers, providing a serene atmosphere conducive to productivity. The property features well-appointed rooms and modern amenities designed to facilitate a seamless stay for guests on work-related trips. With its proximity to local business hubs, it offers convenience without compromising comfort, making it a reliable choice for professionals seeking a peaceful retreat.
  • The Harbor Front Inn: Situated just 2km from Shelter Island Heights, The Harbor Front Inn blends business and leisure in a 3.5-star setting, boasting a commendable guest rating of 8.8 out of 10. Ideal for pet-friendly travel, this inn allows dogs and has specific policies to accommodate pets, including weight limits and fees. Guests can relish the scenic waterfront views while enjoying well-equipped rooms tailored for both relaxation and work. Its combination of convenience and charm makes it a sought-after destination for those balancing business and pleasure.

Where to stay near Shelter Island Heights

Discover the charm of Shelter Island Heights, where outdoor enthusiasts and families alike can revel in its scenic beauty. Stroll through the quaint neighbourhoods, enjoy leisurely bike rides, or relax by the picturesque waterfront. Nearby, explore the captivating Shelter Island community, offering a blend of luxury and budget-friendly options. With its family-friendly atmosphere and numerous excursions, Shelter Island Heights promises an unforgettable getaway in a serene island setting.

  • Greenport: Nestled just 1.6km from Shelter Island Heights, Greenport is a charming city that thrives on its seasonal vibrancy. Visitors flock here primarily between June and August for its delightful outdoor, romantic, and beach experiences. The area is perfect for a range of activities, from relaxing at the beach to enjoying a round of golf at local courses. Greenport boasts lovely parks and hosts music concerts that enhance its lively atmosphere. With picturesque beaches and a welcoming community, it’s an ideal spot for a leisurely day out.
  • Hamptons: Located approximately 16km from Shelter Island Heights, the Hamptons is synonymous with luxury and natural beauty. This iconic coastal region sees a surge in visitors during the summer months, particularly from June to August. Known for its stunning beaches and outdoor recreation, the Hamptons offers a romantic ambiance perfect for couples. You can explore various golf courses or indulge in winter sports like skiing during the off-peak months. With its scenic lakes and family-friendly beaches, the Hamptons is a quintessential getaway destination.
  • Shelter Island: Just 1.6km away from Shelter Island Heights, Shelter Island is a serene city that captures the essence of a tranquil escape. Seasonal visitor numbers peak from June to August, attracting those seeking outdoor adventures and romantic getaways. Guests can enjoy the local golf courses or attend lively music concerts, while the beautiful beaches and lakes provide perfect settings for relaxation. This charming island is a hidden gem, ideal for visitors looking to unwind amid stunning natural surroundings.

Things to do near Shelter Island Heights

Shopping

In Shelter Island Heights, you’ll find charming local shops offering unique gifts and souvenirs. If you're up for a drive, visit the nearby Greenport Village, which boasts a variety of boutiques and artisanal shops, perfect for finding that special item to take home.

Recreation

At the Shelter Island Heights Spa, indulge in rejuvenating massages and holistic treatments amid tranquil surroundings. For outdoor enthusiasts, explore the scenic trails of Mashomack Preserve for hiking and birdwatching, offering a serene connection with nature.

Adventure

Experience the thrill of motor racing at Riverhead Raceway, located 34km from Shelter Island Heights, where adrenaline and speed combine in an exhilarating atmosphere. Alternatively, visit Waterford Speedbowl, 39km away, for another exciting race event amidst a vibrant sporting environment.

Nightlife

Enjoy a relaxed evening at the Sunset Beach Bar overlooking the water, where you can sip cocktails and soak in the serene atmosphere. For a lively vibe, head to the Shelter Island Heights Pavilion for live music and dancing, providing a delightful taste of local culture.

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

Find the best attractions in and around Shelter Island Heights

Shelter Island Heights offers a delightful blend of outdoor activities, family-friendly attractions, and romantic spots, making it an ideal vacation destination. Visitors can explore beautiful beaches, tranquil urban parks, and historic buildings, all while soaking up the local culture. Notable attractions include nearby Fishers Island and the charming town of Shelter Island, perfect for those seeking an enriching outdoor experience.

  • North Main Street Historic District: Explore the charming North Main Street Historic District, located 21km from Shelter Island Heights. This neighbourhood boasts a vibrant atmosphere, featuring picturesque architecture and quaint shops that reflect the area's rich history.
  • Crescent Beach: Enjoy the serene beauty of Crescent Beach, situated right within Shelter Island Heights. This idyllic beach offers a relaxed vibe, perfect for sunbathing, swimming, or simply walking along the sandy shore while taking in the stunning views.
  • Orient Point County Park: Just 13km away, Orient Point County Park is an urban park ideal for families and outdoor enthusiasts. With its expansive green spaces, walking trails, and picnic areas, it’s a lovely spot to unwind and connect with nature.

Best time to go to Shelter Island Heights

The best time to visit Shelter Island Heights is dependent on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are low and weather is mostly sunny with light rain.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January35.6°F (2.0°C)Light RainMostly SunnyLowModerately Low
February35.8°F (2.1°C)Light RainMostly CloudyAverageModerately Low
March39.7°F (4.3°C)Light RainMostly SunnyAverageModerately Low
April47.5°F (8.6°C)Light RainMostly SunnyHighAverage
May55.8°F (13.2°C)Light RainMostly SunnyAverageAverage
June64.9°F (18.3°C)Light RainMostly SunnyHighModerately High
July73.0°F (22.8°C)Light RainMostly SunnyHighModerately High
August73.4°F (23.0°C)Light RainMostly SunnyAverageModerately 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 SunnyLowAverage
December42.1°F (5.6°C)Light RainMostly CloudyLowAverage

The nearest major airports for your trip to Shelter Island Heights

To reach Shelter Island Heights, you have several airport options. John F. Kennedy International Airport (JFK) is situated 130km away, with luxurious hotels nearby such as The William Vale and Arlo Williamsburg, both 18km from the airport. T.F. Green Airport (PVD) in Providence, Rhode Island, is 105km distant, with good choices like the Omni Providence Hotel, located 11km away. Lastly, Westchester County Airport (HPN) is 113km from Shelter Island Heights, offering nearby hotels such as The Opus Westchester, just 6km away, with convenient transportation services available for airport transfers.

Frequently asked questions

Where is the best place to stay in Shelter Island Heights?
The Pridwin Hotel is one of the top choices for your stay based on our traveller data. This hotel offers a full-service spa and a private beach. Two other choices for your stay in the area are Pier Blue Inn Old Saybrook - Essex and Gurney's Montauk Resort & Seawater Spa. See all available top hotels, or vacation rentals in Shelter Island Heights.
If I need to cancel my hotel reservation in Shelter Island Heights, will I receive a refund?
Yes, most hotel bookings are fully refundable if cancelled prior to the accommodation's cancellation deadline, which often is within 24-48 hours of your check-in date. If you have a non-refundable reservation, you might still have the option to cancel and get a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Shelter Island Heights.
What's the best family accommodation in Shelter Island Heights?
The Pridwin Hotel is a hotel with a private beach and a restaurant, and it's a top choice on Expedia for families. Shelter Island House is another good choice for your child-friendly holiday. Also, attractions in the area such as Railroad Museum of Long Island and East End Seaport Maritime Museum are fun for children of all ages. Find more child-friendly accommodations in Shelter Island Heights.
What's the best dog-friendly accommodation option in Shelter Island Heights?
The Chequit is a top hotel for people travelling with their pets, and offers a restaurant and a coffee shop/cafe for its human guests. SEVEN - Shelter Island Guest House is another good option if you're bringing your pet along. See more pet-friendly hotel accommodations in Shelter Island Heights.
What's the best place to stay to stay near the beach in Shelter Island Heights?
The Pridwin Hotel is a top beachfront hotel offering a seasonal outdoor pool and free breakfast, located within a short 1-minute walk of Crescent Beach . See more stays near the beach in Shelter Island Heights.
What's the best accommodation for a golf trip to Shelter Island Heights?
Shelter Island House is a top hotel that has an adjacent golf course and features free WiFi. Other good options to stay near a golf course include House on Chase Creek and SEVEN - Shelter Island Guest House. You can tee off at Shelter Island Country Club during your trip. See more golf hotels in Shelter Island Heights.
What are some accommodation options with pools in Shelter Island Heights?
The Pridwin Hotel is a top hotel with a seasonal outdoor pool, a private beach and a full-service spa. View all hotels with pools in Shelter Island Heights.
What is the best spa hotel in Shelter Island Heights?
The Pridwin Hotel is a top spa hotel featuring a private beach, a fitness centre, a bar and a restaurant. Spend an afternoon at Pridwin Spa where you'll find facials, body scrubs, and Swedish massages and more. See all spa hotels in Shelter Island Heights.
How is it to stay in Shelter Island Heights?
Visitors to Shelter Island Heights will definitely enjoy the beaches. Tourists can also enjoy the city's golf courses, entertainment choices and theatres. A top sight in the area is The Hamptons Beaches. In Shelter Island Heights, there are 43 hotels and other accommodation options to choose from. Find out more about Shelter Island Heights.
What should I do while I'm visiting Shelter Island Heights?
Natural beauty is on display at Sunset Beach, Crescent Beach and Menhadden Lane Beach. Additionally, you'll find The Hamptons Beaches in the area. Take a look at what more there is to see and do in Expedia's Shelter Island Heights guide.
What's the weather like in Shelter Island Heights?
The hottest months are usually August and July, with an average temperature of 21°C, while the coldest months are January and February, with an average of 3°C. Average annual precipitation for Shelter Island Heights is 1452 mm.