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
Shelter Island Heights
United States
Anna
¥78,270
¥98,366 total
includes taxes & fees
Sep 13 - Sep 14
The Pridwin Hotel

2. The Chequit

The Chequit
The Heights
United States
Kristin
¥29,402
¥33,592 total
includes taxes & fees
Oct 7 - Oct 8
The Chequit

3. House on Chase Creek

House on Chase Creek
The Heights
United States
Calvin
¥33,237
¥37,974 total
includes taxes & fees
Oct 5 - Oct 6
House on Chase Creek

4. Shelter Island House

Shelter Island House
Shelter Island Heights
United States
Dorothy
¥31,071
¥35,497 total
includes taxes & fees
Oct 4 - Oct 5
Shelter Island House

5. West Neck Guesthouse

West Neck Guesthouse
Shelter Island Heights
United States
Allie
¥48,401
¥55,299 total
includes taxes & fees
Sep 15 - Sep 16
West Neck Guesthouse

6. Zey Hotel

Zey Hotel
Greenport
United States
Renee
¥26,053
¥29,766 total
includes taxes & fees
Sep 13 - Sep 14
Zey Hotel

7. The Harbor Front Inn

The Harbor Front Inn
Greenport
United States
Michael
¥36,543
¥46,159 total
includes taxes & fees
Oct 4 - Oct 5
The Harbor Front Inn

8. The Menhaden

The Menhaden
Greenport
United States
Lisa
¥61,003
¥75,871 total
includes taxes & fees
Sep 15 - Sep 16
The Menhaden

9. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
Greenport
United States
Sirikhwan
¥42,223
¥48,240 total
includes taxes & fees
Oct 12 - Oct 13
Silver Sands Motel & Beach Bungalows

10. Oyster Estate

Oyster Estate
Greenport
United States
Jenny
¥48,862
¥61,564 total
includes taxes & fees
Oct 7 - Oct 8
Oyster Estate

11. American Beech Hotel

American Beech Hotel
Greenport
United States
Mary
¥47,984
¥60,998 total
includes taxes & fees
Sep 21 - Sep 22
American Beech Hotel

12. Sound View Greenport

Sound View Greenport
Greenport
United States
Irene
¥37,392
¥55,950 total
includes taxes & fees
Sep 28 - Sep 29
Sound View Greenport

13. North Fork Resort

North Fork Resort
Greenport
United States
Lisa
¥45,747
¥52,267 total
includes taxes & fees
Oct 12 - Oct 13
North Fork Resort

14. The Shoals Suites and Slips

The Shoals Suites and Slips
Southold
United States
Melissa
¥31,159
¥39,459 total
includes taxes & fees
Oct 1 - Oct 2
The Shoals Suites and Slips

15. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
United States
Christine
¥44,606
¥64,726 total
includes taxes & fees
Oct 5 - Oct 6
Cliffside Resort Condominiums

16. Sag Harbor Inn

Sag Harbor Inn
Sag Harbor
United States
Loretta
¥50,022
¥57,151 total
includes taxes & fees
Oct 4 - Oct 5
Sag Harbor Inn

17. Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
Old Saybrook
United States
Michael
¥15,617
¥17,959 total
includes taxes & fees
Oct 4 - Oct 5
Quality Inn Old Saybrook - Westbrook

18. Clinton Motel

Clinton Motel
Clinton
United States
Selena
¥11,959
¥13,753 total
includes taxes & fees
Sep 15 - Sep 16
Clinton Motel

19. Lamplighter Motel - Clinton, Connecticut

Lamplighter Motel - Clinton, Connecticut
Clinton
United States
Steven
¥10,579
¥12,166 total
includes taxes & fees
Sep 21 - Sep 22
Lamplighter Motel - Clinton, Connecticut

20. Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex
Saybrook Manor
United States
Carolyn
¥12,597
¥14,487 total
includes taxes & fees
Sep 16 - Sep 17
Pier Blue Inn Old Saybrook - Essex
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Where to stay in Shelter Island Heights

Find the best Shelter Island Heights areas and neighborhoods for the activities you enjoy most.Learn more about Shelter Island Heights
Learn more about Shelter Island Heights

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

Hay Beach might not have many top sights, but Greenport Carousel and Greenport Harbor Brewing Company are two attractions nearby that you can check out.

Stay near popular Shelter Island Heights attractions

Crescent Beach

9.4/10 (13 reviews)
Why not spend a carefree afternoon at Crescent Beach during your travels in Shelter Island Heights? Experience the area's entertainment venues and theater scene.
See properties

Shelter Island Country Club

10.0/10 (3 reviews)
Enjoy a round of golf in Shelter Island Heights at Shelter Island Country Club. Stroll along the beaches or discover the area's sunsets.
See properties

Menhadden Lane Beach

8.8/10 (3 reviews)
Why not spend a carefree afternoon at Menhadden Lane Beach during your travels in Shelter Island Heights?
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Sylvester Manor

8.8/10 (3 reviews)
You can find out about the history of Shelter Island Heights when you stop by Sylvester Manor. Stroll along the beaches or discover the area's sunsets.
See properties

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.

See all hotels in Shelter Island Heights
A pebbled beach with a sunset and a distant bridge.

Top Shelter Island Heights Hotel Reviews

Ocean Surf Resort

Ocean Surf Resort

10/10 Excellent
"Staff friendly. Room clean and comfortable"
Juikuen 2-night trip
Posted 2 hours ago
Ocean Surf Resort
Montauk Blue Hotel

Montauk Blue Hotel

8/10 Good
"chairs forvthe beach"
lorraine 2-night trip
Posted 5 hours ago
Montauk Blue Hotel
The Atlantic Hotel

The Atlantic Hotel

10/10 Excellent
"it was a clean bright comfortable room .Super cozy bed and pillows ,wonderful jacuzzi tub! A nice touch with an espresso machine in the room! Parking was easy and close to everything needed."
Amy 1-night trip
Posted 8 hours ago
The Atlantic Hotel
Offshore Montauk

Offshore Montauk

10/10 Excellent
"Everything"
Tonya 1-night trip
Posted 16 hours ago
Offshore Montauk
Zey Hotel

Zey Hotel

10/10 Excellent
"Such an amazing hotel to stay for the weekend"
Olivia 1-night trip
Posted 3 days ago
Zey Hotel
Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

10/10 Excellent
"Very good"
Iosif 1-night trip
Posted 3 days ago
Gurney's Montauk Resort & Seawater Spa
Montauk Manor

Montauk Manor

10/10 Excellent
"Excellent service, beautiful property, accommodating staff."
Maria 3-night trip
Posted 3 days ago
Montauk Manor
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

10/10 Excellent
"Welcoming, helpful, friendly, professional front desk staff. My room was impeccably clean and tidy. The property is centrally-located with ease of accessibility to main roads and major highways, yet far enough off Boston Post Road to ensure a quiet, peaceful and restful stay. Overall, an outstanding, no-frills property! I look forward to staying here once again!"
Marc 1-night trip
Posted 3 days ago
Pier Blue Inn Old Saybrook - Essex

More cheap stays in Shelter Island Heights

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT
¥12,597
¥14,487 total
Sep 16 - Sep 17
includes taxes & fees
Pier Blue Inn Old Saybrook - Essex
Budget Host East End

Budget Host East End

30 Lake Avenue Riverhead NY
¥13,645
¥15,589 total
Sep 14 - Sep 15
includes taxes & fees
Budget Host East End
Kenny's Tipperary Inn

Kenny's Tipperary Inn

432 West Lake Drive Montauk NY
¥16,595
¥19,718 total
Oct 8 - Oct 9
includes taxes & fees
Kenny's Tipperary Inn
The Atlantic Hotel

The Atlantic Hotel

1655 County Road 39 Southampton NY
¥18,411
¥24,894 total
Oct 1 - Oct 2
includes taxes & fees
7.2/10 Good! (1,003 reviews)
The Atlantic Hotel
Ocean Surf Resort

Ocean Surf Resort

84 South Emerson Avenue Montauk NY
¥19,743
¥29,273 total
Sep 28 - Sep 29
includes taxes & fees
8.6/10 Excellent! (311 reviews)
Ocean Surf Resort
Montauk Blue Hotel

Montauk Blue Hotel

108 South Emerson Avenue Montauk NY
¥19,417
¥29,741 total
Oct 12 - Oct 13
includes taxes & fees
9.2/10 Wonderful! (271 reviews)
Montauk Blue Hotel

Find out more about Shelter Island Heights

Top reasons to visit Shelter Island Heights

  • Scenic Golf Course: Enjoy a round of golf amidst picturesque landscapes at the Shelter Island Country Club.
  • Outdoor Adventures: Explore scenic trails perfect for hiking, biking, and enjoying nature.
  • Beautiful Beaches: Relax on stunning beaches with crystal clear waters, ideal for sunbathing and swimming.
  • Charming Accommodations: Stay in cozy bed & breakfasts and unique agritourism properties offering local hospitality.
  • Historic District: Discover the rich culture and history of Shelter Island Heights through its charming buildings and parks.

Find great hotels near Shelter Island Heights

Discover charming accommodations in Shelter Island Heights, New York, where you can choose from cozy bed & breakfasts and unique agritourism properties. This picturesque destination caters to families and adventure seekers alike, with many pet-friendly options available. Experience the warmth of local hospitality and find the ideal place to unwind while enjoying stunning views and outdoor activities in this serene coastal enclave.

  • Sound View Greenport: Nestled 3km away from Shelter Island Heights, Sound View Greenport is a charming 3.5-star hotel that boasts a guest rating of 8.4 out of 10. This property is ideal for families, beachgoers, and business travelers alike, with direct access to the beach that enhances your vacation experience. Families will appreciate the thoughtful amenities for children, including complimentary cribs and window guards for safety. The hotel’s serene atmosphere combined with its coastal charm makes it a delightful choice for those looking to unwind by the water.
  • Sag Harbor Inn: Located 10km from Shelter Island Heights, Sag Harbor Inn stands out with a remarkable guest rating of 9.4 out of 10. This 3.5-star property is tailored for business travelers seeking a comfortable and professional environment. The inn offers a sophisticated atmosphere, making it easy to blend work and leisure. With its prime location near the historic village of Sag Harbor, guests can enjoy local shops and dining while still having a peaceful retreat to return to at the end of the day.
  • The Harbor Front Inn: Just 2km from Shelter Island Heights, The Harbor Front Inn is a pet-friendly 3.5-star hotel with a guest rating of 8.8 out of 10. This property welcomes furry companions and offers several amenities for pets, including in-room accommodations for a maximum weight limit. Ideal for both business and leisure travelers, the inn provides a cozy atmosphere with stunning waterfront views. Its proximity to local attractions makes it a convenient choice for those looking to explore the area while enjoying the comforts of home.

Where to stay near Shelter Island Heights

Exploring Shelter Island Heights offers a delightful blend of outdoor adventures and family-friendly activities. Nestled in the serene surroundings of Shelter Island, this charming community features picturesque landscapes and romantic spots perfect for couples. Nearby neighborhoods provide a variety of experiences, from luxury getaways to budget-friendly excursions. Whether you're hiking scenic trails or enjoying local dining, Shelter Island Heights promises an unforgettable vacation immersed in nature and hospitality.

  • Greenport: Situated only 2km from Shelter Island Heights, Greenport is a charming coastal village that offers a delightful blend of outdoor activities and romantic settings. Known for its picturesque waterfront, Greenport is perfect for beach lovers and adventure seekers alike. Visitors can enjoy a round of golf, explore recreational areas, or attend live music concerts throughout the year. The local landmarks, including family-friendly beaches and scenic parks, provide ample opportunities for relaxation and exploration. Given its seasonal nature, the best time to experience Greenport’s vibrant atmosphere is from June to August, when traveler numbers peak.
  • Hamptons: Located 16km from Shelter Island Heights, the Hamptons is synonymous with upscale beach living and breathtaking outdoor scenery. This region attracts visitors seeking a blend of relaxation and adventure, with its stunning beaches and recreational opportunities. The Hamptons are famous for their luxurious golf courses and vibrant social scene, particularly during the peak tourist season from June to August. While winter visitors are fewer, the area still offers beautiful landscapes and serene lakes for those looking to escape the hustle and bustle. The charming towns and family beaches make it ideal for a romantic getaway or a fun family vacation.
  • Shelter Island: Just 2km from Shelter Island Heights, Shelter Island is a serene destination that captivates visitors with its natural beauty and outdoor experiences. The island is renowned for its unspoiled beaches and tranquil lakes, making it a perfect spot for romantic strolls or family fun. Seasonal travelers flock to Shelter Island between June and August, enjoying activities like golfing, skiing, and live music concerts. With its inviting atmosphere and proximity to local attractions, Shelter Island promises a relaxing escape from everyday life, especially during the warmer months.

Things to do near Shelter Island Heights

Shopping

In Shelter Island Heights, you can enjoy quaint local shops offering unique gifts and souvenirs. If you're up for a drive, head to the nearby Southold Marketplace for a wider selection of artisanal goods and specialty items.

Recreation

At Shelter Island Heights, unwind at the tranquil Spa at the Chequit, offering rejuvenating treatments and yoga sessions. Explore the picturesque beaches for sunbathing or kayaking, and enjoy scenic bike rides along the waterfront, immersing yourself in the island's natural beauty.

Adventure

Experience the thrill at Riverhead Raceway, located 34km from Shelter Island Heights, where you can enjoy exhilarating motor racing events amidst a vibrant atmosphere. Alternatively, head to Waterford Speedbowl, 39km away, for more high-speed action and adrenaline-pumping excitement in a lively setting.

Nightlife

The nightlife in Shelter Island Heights offers a laid-back yet vibrant atmosphere. Enjoy drinks at the local tavern or take in the scenic views at a waterfront bar. For a lively evening, explore nearby restaurants and lounges that often feature live music and cozy outdoor seating.

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

Find the best attractions near Shelter Island Heights

Whether you're seeking outdoor adventures, family fun, or a romantic getaway, Shelter Island Heights has something for everyone. Explore beautiful beaches, charming urban parks, and historic buildings. Popular attractions include the Shelter Island Country Club and the historic district, perfect for travelers interested in culture and outdoor experiences. Discover the local points of interest and make the most of your visit to this idyllic destination.

  • East Hampton Main Beach: Located 21km from Shelter Island Heights, this beautiful beach offers a quintessential East Coast experience. Enjoy sunbathing, swimming, or strolling along the shoreline while soaking up the vibrant beach vibes. The scenic views and soft sands make it an ideal spot for relaxation and leisure.
  • Orient Point County Park: Just 13km away, this urban park features lush landscapes and family-friendly activities. Enjoy picnicking, hiking, or simply exploring the outdoors. The park's city vibes combine with nature, making it a perfect retreat for families looking for a day of fun.
  • Sag Harbor Marine Park: Located 11km from Shelter Island Heights, this marina offers adventure seekers a chance to explore the water. Engage in activities like kayaking, fishing, or sailing while surrounded by beautiful beach vibes and picturesque views of the marina.

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

Traveling to Shelter Island Heights is convenient with access to several major airports. New York's JFK Airport is 130km away, with upscale hotels nearby such as The William Vale and Arlo Williamsburg, both 18km from the airport. LaGuardia Airport, located 132km away, offers luxury accommodations like Hilton Club The Quin New York and The Plaza, A Fairmont Hotel, both within 10km. Alternatively, Hartford's Bradley International Airport is 98km from Shelter Island Heights, featuring options like DoubleTree by Hilton Hartford and Marriott Hartford Downtown, both providing easy access to the airport. Each hotel offers transportation services for a seamless travel experience.

Frequently asked questions

Where is the best place to stay in Shelter Island Heights?
The Chequit is one of the top choices for your stay based on our traveler data. This hotel offers a restaurant and free parking. Other good choices for your stay include The Pridwin Hotel and West Neck Guesthouse. See all available top hotels, or vacation rentals in Shelter Island Heights.
What's the top vacation rental in Shelter Island Heights?
Unobstructed Ocean Views ! A Beautiful Montauk Getaway: Visitors like this Shelter Island Heights vacation home rental. It is located on the beach and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Kick off your shoes and enjoy yourself with a patio and a garden. See all vacation rentals in Shelter Island Heights.
If I need to cancel my hotel reservation in Shelter Island Heights, will I receive a refund?
Yes, the majority of room reservations are fully refundable provided that you cancel before the hotel's cancellation deadline, which often is within 24-48 hours of your arrival date. If you have a non-refundable reservation, you might still have the option to cancel and be given a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Shelter Island Heights.
Where can I learn more about changing or cancelling my trip to Shelter Island Heights?
For more information about picking new dates or cancelling your trip to Shelter Island Heights, click here.
What's the best place to stay for a family trip to 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 family trip. Attractions in the area like East End Seaport Maritime Museum and Railroad Museum of Long Island are also fun for kids of all ages. Find more child-friendly accommodations in Shelter Island Heights.
What's the best pet-friendly hotel in Shelter Island Heights?
The Chequit is a top hotel for people traveling with their pets, and offers a restaurant and a coffee shop for its human guests. SEVEN - Shelter Island Guest House is another option if you're bringing your pet along. See more pet-friendly hotel accommodations in Shelter Island Heights.
Where is the best hotel to stay near Sunset Beach?
Adjacent to Sunset Beach, Shelter Island House is one of the top choices for your stay based on our traveler data, and this 3.5-star hotel offers free breakfast and a restaurant. Other good choices within a few miles include The Harborfront Inn and House on Chase Creek.
What about the best place to stay close to Crescent Beach?
One of the top choices for your stay is The Pridwin Hotel, located next to Crescent Beach, and this 3-star hotel offers a private beach and free breakfast. The Harborfront Inn and Sound View Greenport are other good choices within a few miles.
What's the best hotel 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 hotel for a golf vacation in 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 accommodations 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 center, 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.
What's the best hotel for staying near John F. Kennedy International Airport (JFK)?
Holiday Inn Express Kennedy Airport is a popular hotel, featuring free breakfast and free WiFi. It's located a short 1.5 mi (2.5 km) from John F. Kennedy Intl. Airport. Other options near the airport are Fairfield Inn by Marriott JFK Airport and Radisson Hotel JFK Airport.
What's it like staying in Shelter Island Heights?
Visitors to Shelter Island Heights are sure to enjoy the beaches. Tourists can also enjoy the city's golf courses, entertainment choices, and theaters. In Shelter Island Heights, there are 45 hotels and other accommodations to choose from. Find out more about Shelter Island Heights.
What is there to see in Shelter Island Heights?
Natural beauty is on display at Sunset Beach, Crescent Beach, and Menhadden Lane Beach. A couple of additional sights to add to your agenda are Shelter Island Country Club and Sylvester Manor. Check out what more 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 temp of 70°F, while the coldest months are January and February with an average of 38°F. Average annual precipitation for Shelter Island Heights is 57 inches.

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