Photo by Erisa Dilo

Find Historic Hotels in Shelter Island Heights, NY

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Pick from 4 Shelter Island Heights Historic Hotels and compare room rates, reviews, and availability. Most hotels are fully refundable.

The Pridwin Hotel
Seasonal outdoor pool, pool umbrellas, sun loungers
The Pridwin Hotel
4.0 star property
9.6 out of 10, Exceptional, (57)
"Fantastic property. Rooms are beautifully appointed, decor is super chic and comfortable. Gorgeous views and amenities. Absolutely enjoyed our second stay at The Pridwin!"
The Pridwin Hotel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Frequently asked questions

What should a history enthusiast expect from a trip to Shelter Island Heights?
The historical places in Shelter Island Heights are likely at the top of your sightseeing list. Why not appreciate the beaches during your visit?
What's the best hotel in Shelter Island Heights to absorb the local history?
Based on our travel knowledge, West Neck Guesthouse is a top 3.5-star B&B for history buffs booking on Expedia, and it features free breakfast and free WiFi. A couple of other options near historic sites include Shelter Island House and The Pridwin Hotel.
How many historical hotels will I find in Shelter Island Heights?
Shelter Island Heights is home to 46 lodging options bookable on Expedia though you won’t find many designated historic hotels.
What are the top historical sites and other places to visit in Shelter Island Heights?
Shelter Island Heights is notable for landmarks like Sylvester Manor. Natural beauty is on display at Sunset Beach, Crescent Beach, and Menhadden Lane Beach. Additionally, you might want to add Shelter Island Country Club to your agenda.
What is a historic hotel like in Shelter Island Heights?
When you book a historic hotel, you’ll sleep someplace that has an official historic designation. A palace, castle, grand home or even an old police station, pub, lodge, or skyscraper can be considered a historic hotel as long as it has special significance. Traditional architecture and period features are typically found in the public spaces and guestrooms of these historic hotels in Shelter Island Heights, giving a historical feel.
What is the difference between a historic hotel and a heritage hotel?
“Heritage hotel” is more common in Asia and Europe, wheareas the term “historic hotel” is more commonly used in the U.S. though overall the terms are quite similar. The architecture and actual building of a historic hotel tends to be the most significant aspect. For a heritage hotel, it’s often the cultural value as well as how it shaped the community.
Do historic hotels in Shelter Island Heights have modern facilities?
Hotels have the safety features and modern conveniences you’ve come to expect, but every effort is made to preserve the historic aspects and traditions. WiFi, heating and air conditioning, updated bathroom facilities, and the popular amenities found at a contemporary hotel will also be available in a historic hotel. Rest assured that when you choose a historic hotel in Shelter Island Heights, you won’t find a place that’s uncomfortable or rundown.