A pebbled beach with a sunset and a distant bridge.

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Our top choices for Shelter Island Heights hotels

1. The Chequit

The Chequit
3.0 star property
The Heights
9.0 out of 10, Wonderful, (75 reviews)
"Friendly staff , Unique property."
United States
Patrick
The price is CA $238
CA $271 total
includes taxes & fees
Nov 19 - Nov 20
The Chequit

2. House on Chase Creek

House on Chase Creek
2.5 star property
The Heights
9.4 out of 10, Exceptional, (87 reviews)
"Such a cute place to stay! Bill was super kind and helpful! I was only in for a quick night but I would definitely stay here again!!"
United States
Tracey
The price is CA $258
CA $295 total
includes taxes & fees
Nov 9 - Nov 10
House on Chase Creek

3. The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
9.0 out of 10, Wonderful, (674 reviews)
"Such a lovely place for a getaway. Charming town and lovely water views!"
United States
Laura
The price is CA $182
CA $248 total
includes taxes & fees
Nov 18 - Nov 19
The Harbor Front Inn

4. Zey Hotel

Zey Hotel
3.5 star property
Greenport
9.2 out of 10, Wonderful, (441 reviews)
"Great location…thoroughly enjoyed our time."
United States
Renee
The price is CA $190
CA $217 total
includes taxes & fees
Nov 10 - Nov 11
Zey Hotel

5. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
Greenport
10.0 out of 10, Exceptional, (187 reviews)
"Nicely renovated and enjoyable."
United States
Becky
The price is CA $300
CA $343 total
includes taxes & fees
Dec 2 - Dec 3
Silver Sands Motel & Beach Bungalows

6. Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very good, (763 reviews)
"The ambience is amazing! We loved our stay!!"
United States
Christine
The price is CA $213
CA $283 total
includes taxes & fees
Nov 15 - Nov 16
Sound View Greenport

7. Oyster Estate

Oyster Estate
4.0 star property
Greenport
9.2 out of 10, Wonderful, (301 reviews)
"incredible stay, pet friendly and very accommodating. Staff was so kind!"
United States
Allison
The price is CA $296
CA $373 total
includes taxes & fees
Dec 2 - Dec 3
Oyster Estate

8. The Shoals Suites and Slips

The Shoals Suites and Slips
3.5 star property
Southold
9.4 out of 10, Exceptional, (349 reviews)
"Very clean property, beautiful view, and quiet."
United States
Masayo
The price is CA $222
CA $288 total
includes taxes & fees
Nov 2 - Nov 3
The Shoals Suites and Slips

9. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (298 reviews)
"Great condo. Very nice location and grounds."
United States
William
The price is CA $236
CA $425 total
includes taxes & fees
Nov 12 - Nov 13
Cliffside Resort Condominiums

10. American Beech Hotel

American Beech Hotel
3.5 star property
Greenport
9.0 out of 10, Wonderful, (208 reviews)
"Great location, very friendly and helpful "
United States
Mary
The price is CA $350
CA $456 total
includes taxes & fees
Nov 2 - Nov 3
American Beech Hotel

11. The Menhaden

The Menhaden
3.5 star property
Greenport
9.6 out of 10, Exceptional, (195 reviews)
"Very clean, excellent staff and excellent location. All of the shops and restaurants are within walking distance, and the wineries a very short cab ride. Really enjoyed staying here and we will absolutely be back."
United States
Daniel
The price is CA $386
CA $497 total
includes taxes & fees
Dec 1 - Dec 2
The Menhaden

12. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (72 reviews)
"Everything was perfect 💞"
United States
Altynai
The price is CA $434
CA $496 total
includes taxes & fees
Nov 9 - Nov 10
North Fork Resort

13. Sag Harbor Inn

Sag Harbor Inn
3.5 star property
Sag Harbor
9.4 out of 10, Exceptional, (683 reviews)
"Free parking, clean, continental breakfast good quality."
United States
Terri
The price is CA $306
CA $350 total
includes taxes & fees
Nov 2 - Nov 3
Sag Harbor Inn

14. Faraway Sag Harbor

Faraway Sag Harbor
4.0 star property
Sag Harbor
9.0 out of 10, Wonderful, (320 reviews)
"Great location , wonderful lobby bar Cute rooms"
United States
Thomas
The price is CA $446
CA $561 total
includes taxes & fees
Nov 16 - Nov 17
Faraway Sag Harbor

15. Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (344 reviews)
"Loved this place. Perfect for a one night stay. What I loved most though, was how clean and fresh the linens were."
United States
Kalev
The price is CA $108
CA $124 total
includes taxes & fees
Nov 2 - Nov 3
Clinton Motel

16. Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex
2.0 star property
Saybrook Manor
8.0 out of 10, Very good, (1,008 reviews)
"Staff was friendly. Grounds very well kept. But rooms are very dated."
United States
Kevin
The price is CA $110
CA $126 total
includes taxes & fees
Nov 17 - Nov 18
Pier Blue Inn Old Saybrook - Essex

17. Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,419 reviews)
"Excellent service, beautiful property, accommodating staff."
United States
Maria
The price is CA $194
CA $249 total
includes taxes & fees
Nov 30 - Dec 1
Montauk Manor

18. The Atlantic Hotel

The Atlantic Hotel
2.5 star property
Southampton
7.2 out of 10, Good, (1,001 reviews)
"Lots of parking, rooms were clean and smelt nice"
United States
miranda
The price is CA $145
CA $200 total
includes taxes & fees
Nov 24 - Nov 25
The Atlantic Hotel

19. Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
Old Saybrook
7.8 out of 10, Good, (1,004 reviews)
"The staff gave us good recommendations for places to eat and things to do"
United States
Susan
The price is CA $135
CA $156 total
includes taxes & fees
Nov 29 - Nov 30
Quality Inn Old Saybrook - Westbrook

20. Water's Edge Resort & Spa

Water's Edge Resort & Spa
3.5 star property
Westbrook Center
8.8 out of 10, Excellent, (1,001 reviews)
"Beautiful setting, good food, friendly staff. Will definitely stay again"
United States
cynthia
The price is CA $247
CA $308 total
includes taxes & fees
Dec 2 - Dec 3
Water's Edge Resort & Spa
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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.

A pebbled beach with a sunset and a distant bridge.

Top Shelter Island Heights Hotel Reviews

More cheap stays in Shelter Island Heights

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 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 $122 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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