Find Historic Hotels in Chester, NY

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Top Chester Historic Hotels

Restaurant
Overlook Lodge at Bear Mountain
Overlook Lodge at Bear Mountain
2.5 star property
8.4 out of 10, Very Good, (1012)
"Clean room, easy parking"
$109 nightly
The price is $124
Nov 12 - Nov 13
Total with taxes and fees
Overlook Lodge at Bear Mountain
Exterior
Hampton Inn Fishkill
Hampton Inn Fishkill
2.5 star property
8.6 out of 10, Excellent, (1002)
"Nice place"
$125 nightly
The price is $142
Oct 30 - Oct 31
Total with taxes and fees
Hampton Inn Fishkill
Fridge, microwave, oven, stovetop
Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer
Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer
10.0 out of 10, Exceptional, (44)
"Great room and location. A nice home base for exploring the area. "
$211 nightly
The price is $243
Nov 11 - Nov 12
Total with taxes and fees
Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer
Property grounds
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, (122)
"It has an incredible mountain and water view. "
$272 nightly
The price is $308
Oct 15 - Oct 16
Total with taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Outdoor pool, a heated pool
Luxurious Ski in-Ski Out Mnt. Creek/Hot tub/Tennis & Pickleball/Heated pool/Golf
Luxurious Ski in-Ski Out Mnt. Creek/Hot tub/Tennis & Pickleball/Heated pool/Golf
9.8 out of 10, Exceptional, (87)
"Such a magical property! I came here with some friends for my birthday weekend and we had the most incredible time. The space- both indoors and out, is even more beautiful than the pictures (which never happens!). Everything was very clean and well kept. And the property manager was very supportive and communicative throughout. Providing lots of helpful information beforehand, and stayed in touch during my stay, even over the smallest things. We came during the summer but would love to come back...
$1,553 nightly
The price is $1,754
Oct 15 - Oct 16
Total with taxes and fees
Luxurious Ski in-Ski Out Mnt. Creek/Hot tub/Tennis & Pickleball/Heated pool/Golf
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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Top Chester Hotel Reviews

Hampton Inn & Suites Mahwah

Hampton Inn & Suites Mahwah

10/10 Excellent
"Close EV charging and parking. Staff was friendly and helpful."
Michael 1-night trip
Posted 20 hours ago
Hampton Inn & Suites Mahwah

Frequently asked questions

What should a history buff expect from a stay in Chester?
You're already probably planning a visit to historical sites during your trip to Chester. During your stay, you can visit the shops and restaurants.
How many historical hotels will I find in Chester?
In Chester, you'll find 19 lodging options bookable on Expedia though not many historic hotels to choose from.
What are the top historical sites and other places to visit in Chester?
Chester is notable for landmarks like Museum Village. In the area, you'll also find LEGOLAND® New York and Woodbury Common Premium Outlets.
What is a historic hotel like in Chester?
When you book a historic hotel, you'll sleep in a building that has an officially recognized national historic designation. A castle, a palace or even a pub or an old police station can be considered a historic hotel provided that it has special significance. Traditional architecture and period features can be admired within the guestrooms or public spaces of these historic hotels in Chester, 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 building of historic hotels are generally the most important aspect. For a heritage hotel, mainly, it's cultural value as well as how it inspired the community.
Do historic hotels in Chester have modern facilities?
Hotels have the safety features and modern conveniences you might expect, but every effort is made to preserve historic facades and treasured traditions. Smart TVs, WiFi, updated bathroom facilities, and the amenities found in most hotels should be available at a historic hotel. Rest assured that when you select a historic hotel in Chester, you won't be staying at a place that's uncomfortable or rundown.

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