A pebbled beach with a sunset and a distant bridge.

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3 Sept - 4 Sept
Tomorrow
4 Sept - 5 Sept
This weekend
4 Sept - 6 Sept
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11 Sept - 13 Sept

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Our top choices for Shelter Island Heights hotels

1. The Chequit

The Chequit
The Heights
United States
Kathleen
AU$310
includes taxes & fees
4 Oct - 5 Oct
The Chequit

2. House on Chase Creek

House on Chase Creek
The Heights
United States
Calvin
AU$392
includes taxes & fees
8 Sept - 9 Sept
House on Chase Creek

3. The Pridwin Hotel

The Pridwin Hotel
Shelter Island Heights
United States
Anna
AU$933
includes taxes & fees
7 Sept - 8 Sept
The Pridwin Hotel

4. Shelter Island House

Shelter Island House
Shelter Island Heights
United States
Dorothy
AU$321
includes taxes & fees
4 Oct - 5 Oct
Shelter Island House

5. West Neck Guesthouse

West Neck Guesthouse
Shelter Island Heights
United States
Allie
AU$500
includes taxes & fees
7 Sept - 8 Sept
West Neck Guesthouse

6. Zey Hotel

Zey Hotel
Greenport
United States
shaun
AU$269
includes taxes & fees
7 Sept - 8 Sept
Zey Hotel

7. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
Greenport
United States
Sol
AU$471
includes taxes & fees
30 Sept - 1 Oct
Silver Sands Motel & Beach Bungalows

8. The Harbor Front Inn

The Harbor Front Inn
Greenport
United States
Michael
AU$421
includes taxes & fees
4 Oct - 5 Oct
The Harbor Front Inn

9. Sound View Greenport

Sound View Greenport
Greenport
United States
Irene
AU$489
includes taxes & fees
28 Sept - 29 Sept
Sound View Greenport

10. The Shoals Suites and Slips

The Shoals Suites and Slips
Southold
United States
Melissa
AU$357
includes taxes & fees
1 Oct - 2 Oct
The Shoals Suites and Slips

11. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
United States
Christine
AU$590
includes taxes & fees
27 Sept - 28 Sept
Cliffside Resort Condominiums

12. North Fork Resort

North Fork Resort
Greenport
United States
Lisa
AU$484
includes taxes & fees
7 Sept - 8 Sept
North Fork Resort

13. American Beech Hotel

American Beech Hotel
Greenport
United States
Mary
AU$551
includes taxes & fees
7 Sept - 8 Sept
American Beech Hotel

14. The Menhaden

The Menhaden
Greenport
United States
Lisa
AU$756
includes taxes & fees
7 Sept - 8 Sept
The Menhaden

15. Oyster Estate

Oyster Estate
Greenport
United States
Jenny
AU$628
includes taxes & fees
7 Sept - 8 Sept
Oyster Estate

16. Sag Harbor Inn

Sag Harbor Inn
Sag Harbor
United States
Loretta
AU$516
includes taxes & fees
4 Oct - 5 Oct
Sag Harbor Inn

17. Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
Old Saybrook
United States
Theresa
AU$162
includes taxes & fees
4 Oct - 5 Oct
Quality Inn Old Saybrook - Westbrook

18. Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex
Saybrook Manor
United States
Carolyn
AU$147
includes taxes & fees
8 Sept - 9 Sept
Pier Blue Inn Old Saybrook - Essex

19. Clinton Motel

Clinton Motel
Clinton
United States
Selena
AU$127
includes taxes & fees
7 Sept - 8 Sept
Clinton Motel

20. The Captain Stannard

The Captain Stannard
Westbrook Center
United States
Deborah
AU$362
includes taxes & fees
7 Sept - 8 Sept
The Captain Stannard
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Our guide on where to stay in Shelter Island Heights

Find the best Shelter Island Heights areas 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

When in Hay Beach, you can plan a visit to Greenport Carousel and Greenport Harbor Brewing Company, some noteworthy sights in the nearby area.

Stay near popular Shelter Island Heights attractions

Crescent Beach

9.4/10 (13 reviews)
Why not spend a care-free afternoon at Crescent Beach during your travels in Shelter Island Heights? Experience the area's entertainment choices and theatre scene.
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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.
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Menhadden Lane Beach

8.8/10 (3 reviews)
Why not spend a care-free 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.
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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 marina with numerous sailboats docked, a large tree in the foreground, and a flagpole with an American flag.
Photo by Brian V. Rowe

Top Shelter Island Heights Hotel Reviews

Recent Reviews in Shelter Island Heights

Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"Waters edge has wonderful staff and beautiful grounds. The food was also amazing."
Emily 1-night trip
Posted 14 hours ago
Water's Edge Resort & Spa
Budget Host East End

Budget Host East End

10/10 Excellent
"Clean room, well maintained, friendly staff."
Olga 3-night trip
Posted 16 hours ago
Budget Host East End
Ocean Surf Resort

Ocean Surf Resort

10/10 Excellent
"Stutaff was kind and the room was clean. It was very nice to be close to the sea. I had a good time. Thank you"
naoko 1-night trip
Posted 20 hours ago
Ocean Surf Resort
Kenny's Tipperary Inn

Kenny's Tipperary Inn

8/10 Good
"Nice hotel and very clean, and the staff were very courteous and helpful. Beach is walking distance right down the road. Perfect location if you're looking for something by the beach."
Demetra 4-night trip
Posted 22 hours ago
Kenny's Tipperary Inn
Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

10/10 Excellent
"Great beachfront property! Spa is amazing!"
Daniel 1-night trip
Posted 2 days ago
Gurney's Montauk Resort & Seawater Spa
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

8/10 Good
"Reasonable price, nice staff, clean rooms. Fills the need for a short stay!"
Julia 1-night trip
Posted 2 days ago
Pier Blue Inn Old Saybrook - Essex
Montauk Yacht Club

Montauk Yacht Club

10/10 Excellent
"This was a beautiful property on the water. We went to celebrate a birthday and it was the perfect location. The bedrooms were large and had high end toiletries. The restaurants on the property were delicious and had excellent service. It's also pretty centrally located and was only a few minutes from the downtown area. Highly recommend this property."
Arabella 1-night trip
Posted 3 days ago
Montauk Yacht Club
The Bentley Hotel Southampton

The Bentley Hotel Southampton

10/10 Excellent
"A well thought out space. Staff is welcoming and helpful. The Room met our expectations. They even offer a beach pass for the Southampton town beach!"
Victoria 1-night trip
Posted 3 days ago
The Bentley Hotel Southampton

More cheap accommodation in Shelter Island Heights

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT
AU$147
8 Sept - 9 Sept
includes taxes & fees
8/10 Very good! (1,000 reviews)
Pier Blue Inn Old Saybrook - Essex
Kenny's Tipperary Inn

Kenny's Tipperary Inn

432 West Lake Drive Montauk NY
AU$192
4 Oct - 5 Oct
includes taxes & fees
8.4/10 Very good! (956 reviews)
Kenny's Tipperary Inn
Budget Host East End

Budget Host East End

30 Lake Avenue Riverhead NY
AU$195
10 Sept - 11 Sept
includes taxes & fees
6.8/10 (873 reviews)
Budget Host East End
The Atlantic Hotel

The Atlantic Hotel

1655 County Road 39 Southampton NY
AU$225
1 Oct - 2 Oct
includes taxes & fees
The Atlantic Hotel
Ocean Surf Resort

Ocean Surf Resort

84 South Emerson Avenue Montauk NY
AU$262
28 Sept - 29 Sept
includes taxes & fees
8.6/10 Excellent! (303 reviews)
Ocean Surf Resort
Montauk Blue Hotel

Montauk Blue Hotel

108 South Emerson Avenue Montauk NY
AU$291
4 Oct - 5 Oct
includes taxes & fees
Montauk Blue Hotel

Frequently asked questions

What is the best area to stay in Shelter Island Heights?
The best area to stay in Shelter Island Heights is the village area itself, particularly around the historic Shelter Island Heights Historic District.This district is the heart of the community, characterised by its historic Victorian homes and tree-lined streets. It's where you'll find most of the island's amenities, including shops, restaurants, and the ferry terminal for easy access to Greenport. The area is very walkable, making it convenient to explore on foot.For couples seeking a relaxing getaway, staying within the historic district offers a quintessential island experience. You'll be close to dining options and can enjoy strolls along the streets admiring the architecture, or head down to Crescent Beach for a peaceful afternoon by the water. Many accommodations here offer a more intimate setting great for two.Families often find the historic district appealing due to its proximity to activities. The village green provides open space for children, and the calm waters of Crescent Beach are suitable for swimming and building sandcastles.
What are the best hotels in Shelter Island Heights that travellers recommend?
One of the best hotels in Shelter Island Heights that travellers recommend is The Pridwin Hotel.The 4-star Pridwin Hotel, with an outstanding 9.6 rating, offers a wonderful experience with its private beach access and a refreshing poolside bar. Guests frequently highlight the beautiful and clean rooms, the amazing amenities, and the great facilities. Many rooms boast breathtaking water and ocean views, and premium bedding and bathrobes add to the comfort. The hotel is conveniently located just 0.4 km from Crescent Beach and 0.9 km from Sunset Beach, making it ideal for beach enthusiasts.
What are the best family hotels in Shelter Island Heights?
For families visiting Shelter Island Heights, The Pridwin Hotel and The Rams Head Inn are both excellent choices.The 4-star Pridwin Hotel, with an outstanding 9.6 rating, is a fantastic option for families. Guests frequently highlight the beautiful and clean rooms, amazing amenities, and great facilities. Families will appreciate amenities such as sofa beds, kids' meals, and a pool with a gate for added safety. Many rooms offer water or ocean views, adding to the relaxing experience. The hotel is also conveniently located near Sunset Beach, just 0.9 km away, and Crescent Beach, a mere 0.4 km away.Another good option is the 4-star Rams Head Inn, rated 7.6. This hotel caters well to families, offering books and games for children, as well as highchairs. Guests can also enjoy a complimentary continental breakfast. It is located 2.5 km from Menhadden Lane Beach.
What are the best spa hotels in Shelter Island Heights?
For a top-tier spa experience in Shelter Island Heights, The Pridwin Hotel is an excellent choice.This 4-star hotel, boasting an impressive 9.6 rating, offers a full-service onsite spa that provides a wide range of treatments, including Swedish massage, deep tissue massage, body wraps, body scrubs, and hydrotherapy treatments. Guests can also enjoy facial treatments, manicures, pedicures, and a steam room. The Pridwin Hotel is conveniently located just 0.4 km from Crescent Beach and 1.6 km from Shelter Island Country Club, making it ideal for those who appreciate beautiful surroundings and nearby recreational activities. Guests frequently praise its beautiful and clean rooms, amazing amenities, great facilities, and delicious food.
What hotels in Shelter Island Heights offer free breakfast?
For hotels in Shelter Island Heights that offer complimentary breakfast, consider The Pridwin Hotel and The Rams Head Inn.The 4-star Pridwin Hotel, with an outstanding 9.6 rating, offers both free breakfast and continental breakfast. Guests frequently mention the beautiful, clean rooms, amazing amenities, and delicious food. This hotel also provides a free ferry terminal shuttle, free self-parking, and free WiFi. It boasts lovely water and ocean views and is conveniently located near Sunset Beach, just 0.9 km away, and Crescent Beach, 0.4 km away.Another option is the 4-star Rams Head Inn, rated 7.6, which also provides free breakfast and continental breakfast. This hotel offers free WiFi, free self-parking, and is situated approximately 2.5 km from Menhadden Lane Beach.
What are the top pet-friendly hotels in Shelter Island Heights?
For top pet-friendly accommodation in Shelter Island Heights, consider The Rams Head Inn.The 4-star Rams Head Inn, with a rating of 7.6, warmly welcomes pets, specifically dogs. This charming inn offers a delightful dining experience for couples and is conveniently located just 2.5 kilometres from Menhadden Lane Beach.
What are the most romantic hotels in Shelter Island Heights for couples?
For a romantic getaway in Shelter Island Heights, couples should consider The Pridwin Hotel or The Rams Head Inn.The 4-star Pridwin Hotel, with an impressive 9.6 rating, is a beautiful option. Guests frequently praise its amazing amenities, great facilities, and delicious food. Many rooms offer lovely water or ocean views, and the hotel provides complimentary breakfast, including a continental option, and free toiletries. It is conveniently located just 0.4 km from Crescent Beach and 1.6 km from Shelter Island Country Club, making it easy to explore the surroundings.Another option is the 4-star Rams Head Inn, rated 7.6, which features couples' dining. This hotel offers complimentary continental breakfast and free toiletries, along with free self-parking. It is located 2.5 km from Menhadden Lane Beach, providing a quiet setting for a romantic escape.
What are the best hotels in Shelter Island Heights near Crescent Beach?
For hotels in Shelter Island Heights near Crescent Beach, The Pridwin Hotel is an excellent choice.The 4-star Pridwin Hotel, with an impressive rating of 9.6, is located just 0.4 km from Crescent Beach. Guests consistently praise its beautiful and clean rooms, amazing amenities, and great facilities. The hotel also boasts delightful food, and its location is frequently highlighted as a major positive. Many rooms offer water or ocean views, and there is a pool available.
When is the best time to go to Shelter Island Heights?
The best time to go to Shelter Island Heights is during the summer months, from June to September, when the weather is warm and the island is fully operational.During this period, all the island's amenities, including restaurants, shops, and recreational activities, are open and readily available. The ferry service also runs more frequently, making travel to and from the island very convenient. This time of year is superb for those looking to enjoy the beaches and outdoor activities.For those who prefer a quieter experience with pleasant weather, late spring (May) and early autumn (October) are also excellent choices. The crowds are smaller, but the weather is still generally mild enough to enjoy walking, cycling, and the island's natural beauty.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if cancelled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Shelter Island Heights.
How can I save on a hotel booking in Shelter Island Heights with Expedia?
One Key™—Expedia's free travel rewards program—gives you instant access to discounts with Member Prices on Shelter Island 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 Shelter Island Heights?
Prices for hotels in Shelter Island Heights often vary, but you can find a great deal from AU$127 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for our cheapest rates.

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