A pebbled beach with a sunset and a distant bridge.

Find hotels in Shelter Island Heights, NY from CA $110

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Sep 16 - Sep 17
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Our top choices for Shelter Island Heights hotels

1. The Chequit

The Chequit
The Heights
United States
Kristin
CA $279
CA $319 total
includes taxes & fees
Oct 4 - Oct 5
The Chequit

2. House on Chase Creek

House on Chase Creek
The Heights
United States
Calvin
CA $299
CA $342 total
includes taxes & fees
Oct 5 - Oct 6
House on Chase Creek

3. Shelter Island House

Shelter Island House
Shelter Island Heights
United States
Dorothy
CA $280
CA $320 total
includes taxes & fees
Oct 4 - Oct 5
Shelter Island House

4. The Pridwin Hotel

The Pridwin Hotel
Shelter Island Heights
United States
Morris
CA $708
CA $889 total
includes taxes & fees
Sep 17 - Sep 18
The Pridwin Hotel

5. West Neck Guesthouse

West Neck Guesthouse
Shelter Island Heights
United States
Allie
CA $436
CA $498 total
includes taxes & fees
Sep 17 - Sep 18
West Neck Guesthouse

6. Zey Hotel

Zey Hotel
Greenport
United States
Renee
CA $235
CA $268 total
includes taxes & fees
Sep 23 - Sep 24
Zey Hotel

7. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
Greenport
United States
Sirikhwan
CA $388
CA $444 total
includes taxes & fees
Oct 12 - Oct 13
Silver Sands Motel & Beach Bungalows

8. The Harbor Front Inn

The Harbor Front Inn
Greenport
United States
Jordan
CA $325
CA $410 total
includes taxes & fees
Oct 15 - Oct 16
The Harbor Front Inn

9. The Shoals Suites and Slips

The Shoals Suites and Slips
Southold
United States
Melissa
CA $281
CA $355 total
includes taxes & fees
Oct 1 - Oct 2
The Shoals Suites and Slips

10. Sound View Greenport

Sound View Greenport
Greenport
United States
Irene
CA $332
CA $419 total
includes taxes & fees
Oct 1 - Oct 2
Sound View Greenport

11. American Beech Hotel

American Beech Hotel
Greenport
United States
Mary
CA $332
CA $435 total
includes taxes & fees
Sep 22 - Sep 23
American Beech Hotel

12. The Menhaden

The Menhaden
Greenport
United States
Lisa
CA $476
CA $599 total
includes taxes & fees
Sep 17 - Sep 18
The Menhaden

13. North Fork Resort

North Fork Resort
Greenport
United States
Harold
CA $417
CA $476 total
includes taxes & fees
Sep 22 - Sep 23
North Fork Resort

14. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
United States
Christine
CA $402
CA $583 total
includes taxes & fees
Oct 5 - Oct 6
Cliffside Resort Condominiums

15. Oyster Estate

Oyster Estate
Greenport
United States
Matthew
CA $440
CA $554 total
includes taxes & fees
Oct 13 - Oct 14
Oyster Estate

16. Clinton Motel

Clinton Motel
Clinton
United States
Selena
CA $110
CA $126 total
includes taxes & fees
Sep 17 - Sep 18
Clinton Motel

17. Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex
Saybrook Manor
United States
Carolyn
CA $113
CA $130 total
includes taxes & fees
Sep 20 - Sep 21
Pier Blue Inn Old Saybrook - Essex

18. Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
Old Saybrook
United States
Michael
CA $141
CA $162 total
includes taxes & fees
Oct 6 - Oct 7
Quality Inn Old Saybrook - Westbrook

19. Sag Harbor Inn

Sag Harbor Inn
Sag Harbor
United States
Loretta
CA $450
CA $514 total
includes taxes & fees
Oct 4 - Oct 5
Sag Harbor Inn

20. Lamplighter Motel - Clinton, Connecticut

Lamplighter Motel - Clinton, Connecticut
Clinton
United States
Steven
CA $96
CA $110 total
includes taxes & fees
Sep 22 - Sep 23
Lamplighter Motel - Clinton, Connecticut
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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 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.
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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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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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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 pebbled beach with a sunset and a distant bridge.

Top Shelter Island Heights Hotel Reviews

Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"It was the perfect getaway- close to home. The property was beautiful, clean and peaceful. The beach could have been cleaner, but overall we loved our stay. The food served in their variety of restaurants was delicious. We will definitely return."
Jennifer 3-night trip
Posted 9 hours ago
Water's Edge Resort & Spa
Ocean Surf Resort

Ocean Surf Resort

8/10 Good
"The view is the best! Beach is beautiful. Rooms are clean however the rooms need some maintenance done. Holes in doors and curtain rods almost falling down . Air conditioning units need to be replaced. Fans on high all the time and turn on and off every 10 min. Had to turn off at night . The staff are very helpful and courteous. We will return again"
michelle 1-night trip
Posted 10 hours ago
Ocean Surf Resort
Marram

Marram

10/10 Excellent
"Amazing hip on the beach Cool best food anywhere"
Peter 1-night trip
Posted 11 hours ago
Marram
The Atlantic Hotel

The Atlantic Hotel

10/10 Excellent
"I had room facing the busy street, but the room was well insulated and I did not hear the traffic from outside. Also, the floor plan was very functional. Linen was clean CLEAN, bed was SO comfortable And the amenities of small fridge, coffee maker, iron, -and 2 water bottles provided with each room clean was especially helpful. Parking spaces were wide with ample space to unload and open passenger doors."
barbara 5-night trip
Posted 13 hours ago
The Atlantic Hotel
Montauk Manor

Montauk Manor

10/10 Excellent
"Staff was great. Pool and property clean. Location excellent too"
Jean 3-night trip
Posted 1 day ago
Montauk Manor
Sound View Greenport

Sound View Greenport

10/10 Excellent
"Great place on the water. Piano Bar is nice; good food & drink. All the staff was very friendly and helpful."
Joseph 3-night trip
Posted 1 day ago
Sound View Greenport
Sun N Sound

Sun N Sound

8/10 Good
"Very nice and clean. Pool was excellent. Only complaint was that the bathroom sink and shower drains were slow to drain. I'll give it a 8/10"
Kathy 2-night trip
Posted 2 days ago
Sun N Sound
North Fork Resort

North Fork Resort

10/10 Excellent
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
Harold 1-night trip
Posted 2 days ago
North Fork Resort
Zey Hotel

Zey Hotel

10/10 Excellent
"My Husband Phil & I had the Best Stay. Very Quaint Hotel, just a couple of blocks from waterfront.Absolutely spotless, so many sitting areas, Coffee, tea water and ice available 24-7. Our room was spotless, decorated so well. We also had a balcony. James and all staff were so Pleasant and so accommodating. Can't wait to return for another stay. Thank you James .. Phil & Jenn"
Jennifer 1-night trip
Posted 2 days ago
Zey Hotel

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
CA $113
CA $130 total
Sep 20 - Sep 21
includes taxes & fees
8/10 Very good! (1,000 reviews)
Pier Blue Inn Old Saybrook - Essex
Budget Host East End

Budget Host East End

30 Lake Avenue Riverhead NY
CA $124
CA $141 total
Sep 17 - Sep 18
includes taxes & fees
6.8/10 (886 reviews)
Budget Host East End
Kenny's Tipperary Inn

Kenny's Tipperary Inn

432 West Lake Drive Montauk NY
CA $149
CA $178 total
Oct 8 - Oct 9
includes taxes & fees
8.4/10 Very good! (961 reviews)
Kenny's Tipperary Inn
The Atlantic Hotel

The Atlantic Hotel

1655 County Road 39 Southampton NY
CA $166
CA $224 total
Oct 5 - Oct 6
includes taxes & fees
7.2/10 Good! (1,007 reviews)
The Atlantic Hotel
Ocean Surf Resort

Ocean Surf Resort

84 South Emerson Avenue Montauk NY
CA $174
CA $260 total
Sep 29 - Sep 30
includes taxes & fees
8.6/10 Excellent! (316 reviews)
Ocean Surf Resort
Montauk Blue Hotel

Montauk Blue Hotel

108 South Emerson Avenue Montauk NY
CA $201
CA $297 total
Sep 27 - Sep 28
includes taxes & fees
Montauk Blue Hotel

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 $110 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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