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
The Heights
United States
Patrick
CA $218
CA $249 total
includes taxes & fees
Nov 11 - Nov 12
The Chequit

2. House on Chase Creek

House on Chase Creek
The Heights
United States
Tracey
CA $264
CA $301 total
includes taxes & fees
Nov 2 - Nov 3
House on Chase Creek

3. Shelter Island House

Shelter Island House
Shelter Island Heights
United States
Dorothy
CA $287
CA $328 total
includes taxes & fees
Oct 12 - Oct 13
Shelter Island House

4. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
Greenport
United States
Keith
CA $327
CA $374 total
includes taxes & fees
Nov 2 - Nov 3
Silver Sands Motel & Beach Bungalows

5. The Harbor Front Inn

The Harbor Front Inn
Greenport
United States
Antrii
CA $230
CA $303 total
includes taxes & fees
Nov 2 - Nov 3
The Harbor Front Inn

6. Zey Hotel

Zey Hotel
Greenport
United States
Renee
CA $260
CA $297 total
includes taxes & fees
Oct 12 - Oct 13
Zey Hotel

7. Sound View Greenport

Sound View Greenport
Greenport
United States
Irene
CA $243
CA $319 total
includes taxes & fees
Nov 4 - Nov 5
Sound View Greenport

8. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
United States
Christine
CA $241
CA $433 total
includes taxes & fees
Nov 1 - Nov 2
Cliffside Resort Condominiums

9. Oyster Estate

Oyster Estate
Greenport
United States
Allison
CA $321
CA $405 total
includes taxes & fees
Nov 8 - Nov 9
Oyster Estate

10. The Shoals Suites and Slips

The Shoals Suites and Slips
Southold
United States
Melissa
CA $345
CA $430 total
includes taxes & fees
Nov 1 - Nov 2
The Shoals Suites and Slips

11. American Beech Hotel

American Beech Hotel
Greenport
United States
Mary
CA $358
CA $466 total
includes taxes & fees
Oct 12 - Oct 13
American Beech Hotel

12. North Fork Resort

North Fork Resort
Greenport
United States
Harold
CA $342
CA $391 total
includes taxes & fees
Oct 22 - Oct 23
North Fork Resort

13. The Menhaden

The Menhaden
Greenport
United States
Lisa
CA $493
CA $620 total
includes taxes & fees
Nov 9 - Nov 10
The Menhaden

14. Sag Harbor Inn

Sag Harbor Inn
Sag Harbor
United States
Terri
CA $312
CA $357 total
includes taxes & fees
Nov 1 - Nov 2
Sag Harbor Inn

15. The Bentley Hotel Southampton

The Bentley Hotel Southampton
Southampton
United States
Frank
CA $204
CA $233 total
includes taxes & fees
Oct 28 - Oct 29
The Bentley Hotel Southampton

16. Shorewood Inn

Shorewood Inn
Riverhead
United States
Dennis
CA $146
CA $167 total
includes taxes & fees
Oct 12 - Oct 13
Shorewood Inn

17. Offshore Montauk

Offshore Montauk
Montauk
United States
Mary
CA $182
CA $289 total
includes taxes & fees
Nov 2 - Nov 3
Offshore Montauk

18. Ocean Vista Resort

Ocean Vista Resort
Amagansett
United States
Dan
CA $206
CA $235 total
includes taxes & fees
Oct 12 - Oct 13
Ocean Vista Resort

19. Clinton Motel

Clinton Motel
Clinton
United States
Brittany
CA $111
CA $128 total
includes taxes & fees
Oct 13 - Oct 14
Clinton Motel

20. Hyatt Place Long Island East End

Hyatt Place Long Island East End
Riverhead
United States
Susan
CA $191
CA $218 total
includes taxes & fees
Nov 3 - Nov 4
Hyatt Place Long Island East End
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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

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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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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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

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

Sun N Sound

Sun N Sound

10/10 Excellent
"Perfect in every way. The view is spectacular. Amazing sunsets. Well equipped kitchen if you are eating in. Plenty of parking. The housekeepers keep the place super clean. Wonderful place to just enjoy the ocean breeze."
Anna 5-night trip
Posted 2 hours ago
Sun N Sound
Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

10/10 Excellent
"Exceptional service. Always a pleasure to visit!"
Amanda 1-night trip
Posted 2 hours ago
Gurney's Montauk Resort & Seawater Spa
Montauk Blue Hotel

Montauk Blue Hotel

10/10 Excellent
"The only issue was that the TV in the room didn’t work Everything else was great"
keith 1-night trip
Posted 18 hours ago
Montauk Blue Hotel
Ocean Vista Resort

Ocean Vista Resort

10/10 Excellent
"Ocean Vista was a very well-maintained property. Staff was very welcoming and pleasant as well as professional. Enjoyed our stay we’ll go back."
JEAN-LUC 2-night trip
Posted 1 day ago
Ocean Vista Resort
Montauk Yacht Club

Montauk Yacht Club

10/10 Excellent
"Montauk Yacht Club was the perfect getaway for my boyfriend and I to celebrate our 3 year anniversary. Our room was spotless and had a great view of the water. We did mention to them ahead of time that it was our anniversary, thinking they might have some champagne or something waiting in the room for us, but they did not. Nonetheless, it was still a perfect stay. We played tennis and the courts were beautiful. The on-site restaurant was very yummy as well! I definitely recommend coming during the off season, as it is way less crowded in town and very relaxing."
Sarah 3-night trip
Posted 7 days ago
Montauk Yacht Club
Ocean Surf Resort

Ocean Surf Resort

10/10 Excellent
"Perfect for weekend stay"
DAWN 1-night trip
Posted 7 days ago
Ocean Surf Resort

More cheap stays in Shelter Island Heights

Aderi Hotel Niantic

Aderi Hotel Niantic

239 Flanders Road Niantic CT
CA $103
CA $119 total
Nov 11 - Nov 12
includes taxes & fees
Aderi Hotel Niantic
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT
CA $124
CA $143 total
Oct 13 - Oct 14
includes taxes & fees
Pier Blue Inn Old Saybrook - Essex
Budget Host East End

Budget Host East End

30 Lake Avenue Riverhead NY
CA $127
CA $145 total
Oct 12 - Oct 13
includes taxes & fees
Budget Host East End
Sleep Inn & Suites Niantic North

Sleep Inn & Suites Niantic North

5 King Arthur Dr Niantic CT
CA $144
CA $166 total
Nov 1 - Nov 2
includes taxes & fees
Sleep Inn & Suites Niantic North
The Atlantic Hotel

The Atlantic Hotel

1655 County Road 39 Southampton NY
CA $153
CA $210 total
Oct 28 - Oct 29
includes taxes & fees
The Atlantic Hotel
The Bentley Hotel Southampton

The Bentley Hotel Southampton

161 Hills Station Rd Southampton NY
CA $204
CA $233 total
Oct 28 - Oct 29
includes taxes & fees
The Bentley Hotel Southampton

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 $119 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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