Find hotels in Shelter Island Heights, NY from CA $125

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Our top choices for Shelter Island Heights hotels

The Pridwin Hotel

The Pridwin Hotel
4.0 star property
Shelter Island Heights
9.6 out of 10, Exceptional, (85 reviews)
"Overall the places is nice, clean and great views"
United States
Dianne
The price is CA $440
CA $553 total
includes taxes & fees
May 17 - May 18
The Pridwin Hotel

House on Chase Creek

House on Chase Creek
2.5 star property
The Heights
9.4 out of 10, Exceptional, (82 reviews)
"Bill is a wonderful and knowledgeable host for a beautiful getaway in a unique setting."
United States
Robert
The price is CA $378
CA $431 total
includes taxes & fees
May 13 - May 14
House on Chase Creek

West Neck Guesthouse

West Neck Guesthouse
3.5 star property
Shelter Island Heights
8.0 out of 10, Very good, (37 reviews)
"Great property! Close to beach and super clean. "
United States
Leslie
The price is CA $299
CA $342 total
includes taxes & fees
May 31 - Jun 1
West Neck Guesthouse

Shelter Island House

Shelter Island House
3.5 star property
Shelter Island Heights
8.4 out of 10, Very good, (57 reviews)
"One staff member was there to check us in. He was helpful in bringing our bags to our room. He also suggested several restaurants for us to try."
United States
Joseph
The price is CA $275
CA $314 total
includes taxes & fees
May 17 - May 18
Shelter Island House

Marram

Marram
4.0 star property
Montauk
8.8 out of 10, Excellent, (253 reviews)
"Beautiful resort in a great location "
United States
Nikki
The price is CA $427
CA $761 total
includes taxes & fees
May 26 - May 27
Marram

The Surf Club

The Surf Club
3.5 star property
Montauk
8.6 out of 10, Excellent, (281 reviews)
"Quiet, relaxing place to stay, great access to the beach and town!"
United States
Erica
The price is CA $229
CA $336 total
includes taxes & fees
May 19 - May 20
The Surf Club

The Montauk Beach House

The Montauk Beach House
3.5 star property
Downtown Montauk
8.8 out of 10, Excellent, (143 reviews)
"Super staff and beautiful location!"
United States
heather
The price is CA $349
CA $398 total
includes taxes & fees
May 19 - May 20
The Montauk Beach House

Montauk Yacht Club

Montauk Yacht Club
4.0 star property
Montauk
8.6 out of 10, Excellent, (1,006 reviews)
"Great stay. "
United States
Jeanne
The price is CA $394
CA $606 total
includes taxes & fees
Jun 1 - Jun 2
Montauk Yacht Club

Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (426 reviews)
"Awesome room!!! Wish I could come back in the summer"
United States
Nicki
The price is CA $225
CA $272 total
includes taxes & fees
May 13 - May 14
Montauk Oceanside Suites

Montauk Blue Hotel

Montauk Blue Hotel
2.0 star property
Downtown Montauk
9.2 out of 10, Wonderful, (198 reviews)
"Great location "
United States
Regina
The price is CA $329
CA $428 total
includes taxes & fees
May 26 - May 27
Montauk Blue Hotel

Daunt's Albatross Motel

Daunt's Albatross Motel
2.0 star property
Downtown Montauk
9.0 out of 10, Wonderful, (310 reviews)
"Comfortable rooms - wonderfully located with warm and welcoming staff."
United States
Laura
The price is CA $245
CA $280 total
includes taxes & fees
May 14 - May 15
Daunt's Albatross Motel

Solé Beach

Solé Beach
3.0 star property
Downtown Montauk
7.4 out of 10, Good, (104 reviews)
"Great stay! "
United States
Jill
The price is CA $218
CA $250 total
includes taxes & fees
May 13 - May 14
Solé Beach

A Wave Inn

A Wave Inn
2.5 star property
Downtown Montauk
7.6 out of 10, Good, (135 reviews)
"It’s was a really nice place for the price, everything is walking distance, nice spot."
United States
Giordan
The price is CA $113
CA $235 total
includes taxes & fees
May 19 - May 20
A Wave Inn

Ocean Resort Inn

Ocean Resort Inn
2.0 star property
Downtown Montauk
9.6 out of 10, Exceptional, (492 reviews)
"Great friendly start, excellent location and lovely place to stay "
United Kingdom
Phillip
The price is CA $171
CA $195 total
includes taxes & fees
May 13 - May 14
Ocean Resort Inn

Ocean Surf Resort

Ocean Surf Resort
2.0 star property
Downtown Montauk
8.4 out of 10, Very good, (239 reviews)
"We’ve stayed at this hotel before in the winter and it was a great. This time we were staying there and there was no heat. All they had was a small space heater for the room. Fortunately the front desk gave us a refund and we went to another hotel but just know there isn’t heat in the rooms in the winter except a space heater."
United States
Laura
The price is CA $347
CA $397 total
includes taxes & fees
May 26 - May 27
Ocean Surf Resort

Aqualina Inn Montauk

Aqualina Inn Montauk
2.5 star property
Downtown Montauk
9.6 out of 10, Exceptional, (496 reviews)
"Pretty typical refurbished motel in a beach town. One block away from beach - five minute walk to get coffee or grab and go type food. Hot water in shower was a bit erratic, as was the wifi."
United States
Jason
The price is CA $171
CA $195 total
includes taxes & fees
May 13 - May 14
Aqualina Inn Montauk

Offshore Montauk

Offshore Montauk
2.0 star property
Montauk
9.4 out of 10, Exceptional, (132 reviews)
"Very nice rooms! Clean and the location is great! "
United States
Jeremy
The price is CA $251
CA $443 total
includes taxes & fees
May 14 - May 15
Offshore Montauk

Harborside Motel

Harborside Motel
2.5 star property
Culloden Shores
8.8 out of 10, Excellent, (124 reviews)
"Great choice if you’ve spent the whole day exploring Long Island and Montauk, taken in a ton of impressions, and all you want is to sit down for dinner with your group, relax, and crash for the night. My friends and I had a 5/5 experience. We really enjoyed everything."
United States
Serhii
The price is CA $212
CA $242 total
includes taxes & fees
May 13 - May 14
Harborside Motel

Hero Beach Club

Hero Beach Club
4.0 star property
Montauk
9.0 out of 10, Wonderful, (204 reviews)
"Great weekend trip "
United States
Timothy
The price is CA $269
CA $446 total
includes taxes & fees
May 18 - May 19
Hero Beach Club

Kenny's Tipperary Inn

Kenny's Tipperary Inn
2.0 star property
Culloden Shores
8.4 out of 10, Very good, (892 reviews)
"Great stay. Clean rooms. Convenient location. Came in clutch for a last minute reservation when we had to switch hotels."
United States
Laura
The price is CA $173
CA $205 total
includes taxes & fees
May 13 - May 14
Kenny's Tipperary Inn
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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.

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 Gardiner's Bay Country Club and Greenport Carousel are two attractions nearby that you can check out.

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.

Photo by Brian V. Rowe
Open Photo by Brian V. Rowe

Top Shelter Island Heights Hotel Reviews

Recent Reviews in Shelter Island Heights

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Hotels in Shelter Island Heights with star rating

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. Find more child-friendly accommodations in Shelter Island Heights
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. See all spa hotels in Shelter Island Heights
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. Find more hotels with free breakfast in Shelter Island Heights
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. See more pet-friendly hotels in Shelter Island Heights
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. See all romantic hotels in Shelter Island Heights
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 canceled 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 Shelter Island Heights hotel booking with Expedia?
Members always get our best prices. Find our best Shelter Island Heights hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.
How much is the nightly rate at a Shelter Island Heights hotel?
Prices for hotels in Shelter Island Heights often vary, but you can find a great deal from CA $125 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 the cheapest rate.

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