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 $181
CA $207 total
includes taxes & fees
Nov 5 - Nov 6
The Chequit

2. House on Chase Creek

House on Chase Creek
The Heights
United States
Tracey
CA $263
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 7 - Oct 8
Shelter Island House

4. The Harbor Front Inn

The Harbor Front Inn
Greenport
United States
Joseph
CA $211
CA $282 total
includes taxes & fees
Nov 1 - Nov 2
The Harbor Front Inn

5. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
Greenport
United States
Keith
CA $403
CA $460 total
includes taxes & fees
Oct 21 - Oct 22
Silver Sands Motel & Beach Bungalows

6. Zey Hotel

Zey Hotel
Greenport
United States
Renee
CA $240
CA $275 total
includes taxes & fees
Oct 7 - Oct 8
Zey Hotel

7. Sound View Greenport

Sound View Greenport
Greenport
United States
Irene
CA $251
CA $328 total
includes taxes & fees
Nov 4 - Nov 5
Sound View Greenport

8. The Shoals Suites and Slips

The Shoals Suites and Slips
Southold
United States
Melissa
CA $288
CA $364 total
includes taxes & fees
Nov 1 - Nov 2
The Shoals Suites and Slips

9. 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

10. Oyster Estate

Oyster Estate
Greenport
United States
Allison
CA $348
CA $438 total
includes taxes & fees
Nov 1 - Nov 2
Oyster Estate

11. American Beech Hotel

American Beech Hotel
Greenport
United States
Mary
CA $357
CA $465 total
includes taxes & fees
Oct 7 - Oct 8
American Beech Hotel

12. North Fork Resort

North Fork Resort
Greenport
United States
Harold
CA $354
CA $405 total
includes taxes & fees
Oct 13 - Oct 14
North Fork Resort

13. The Menhaden

The Menhaden
Greenport
United States
Lisa
CA $492
CA $620 total
includes taxes & fees
Nov 4 - Nov 5
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
Rich
CA $205
CA $234 total
includes taxes & fees
Oct 14 - Oct 15
The Bentley Hotel Southampton

16. Ocean Vista Resort

Ocean Vista Resort
Amagansett
United States
Dan
CA $181
CA $206 total
includes taxes & fees
Oct 12 - Oct 13
Ocean Vista Resort

17. Water's Edge Resort & Spa

Water's Edge Resort & Spa
Westbrook Center
United States
Toni and Zak
CA $223
CA $281 total
includes taxes & fees
Nov 1 - Nov 2
Water's Edge Resort & Spa

18. Sun N Sound

Sun N Sound
Culloden Shores
United States
MARSILDA
CA $166
CA $213 total
includes taxes & fees
Nov 1 - Nov 2
Sun N Sound

19. Shorewood Inn

Shorewood Inn
Riverhead
United States
Heather
CA $122
CA $139 total
includes taxes & fees
Oct 7 - Oct 8
Shorewood Inn

20. Hamlet Inn

Hamlet Inn
Southampton
United States
Thomas
CA $159
CA $206 total
includes taxes & fees
Oct 7 - Oct 8
Hamlet 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

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.
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

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

10/10 Excellent
"Great"
Linda 2-night trip
Posted less than an hour ago
Gurney's Montauk Resort & Seawater Spa
Ocean Vista Resort

Ocean Vista Resort

10/10 Excellent
"."
andrew 1-night trip
Posted 7 hours ago
Ocean Vista Resort
Ocean Resort Inn

Ocean Resort Inn

10/10 Excellent
"Nice room close to beach"
Christina 2-night trip
Posted 8 hours ago
Ocean Resort Inn
The Bentley Hotel Southampton

The Bentley Hotel Southampton

10/10 Excellent
"Very nice"
Rich 1-night trip
Posted 9 hours ago
The Bentley Hotel Southampton
The Atlantic Hotel

The Atlantic Hotel

8/10 Good
"My only complaint would be i wish there was a Keurig machine in the room instead of an espresso machine. Would definitely stay there again."
Fred 2-night trip
Posted 11 hours ago
The Atlantic Hotel
Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"Scenery was picture postcard perfect! Highly recommend balcony view from the main hotel Room service was excellent and the dining room staff and food were wonderful Only downside. There were no robes in the room and if you drank the bottled water, you were charged. Not really disclosed very well I'm actually planning on going back"
Billie 2-night trip
Posted 12 hours ago
Water's Edge Resort & Spa
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 1 day ago
Montauk Yacht Club
Montauk Blue Hotel

Montauk Blue Hotel

8/10 Good
"Great location!"
Melissa 2-night trip
Posted 1 day ago
Montauk Blue Hotel
Ocean Surf Resort

Ocean Surf Resort

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

More cheap stays in Shelter Island Heights

Aderi Hotel Niantic

Aderi Hotel Niantic

239 Flanders Road Niantic CT
CA $100
CA $115 total
Nov 5 - Nov 6
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 $116
CA $134 total
Oct 12 - Oct 13
includes taxes & fees
8/10 Very good! (1,006 reviews)
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 7 - Oct 8
includes taxes & fees
6.8/10 (894 reviews)
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
Oct 26 - Oct 27
includes taxes & fees
Sleep Inn & Suites Niantic North
The Atlantic Hotel

The Atlantic Hotel

1655 County Road 39 Southampton NY
CA $127
CA $181 total
Oct 28 - Oct 29
includes taxes & fees
7.2/10 Good! (1,005 reviews)
The Atlantic Hotel
The Bentley Hotel Southampton

The Bentley Hotel Southampton

161 Hills Station Rd Southampton NY
CA $205
CA $234 total
Oct 14 - Oct 15
includes taxes & fees
9.6/10 Exceptional! (594 reviews)
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 $115 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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