Book the Best HISTORIC Hotels in Chester in 2026

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Our top choices for Chester historic hotels

1. Overlook Lodge at Bear Mountain

Bear Mountain

randall

CA $152

CA $187 total

includes taxes & fees

Sep 23 - Sep 24

1 bedroom, desk, iron/ironing board, WiFi (free)

2. Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Fort Montgomery

Jasmine

CA $277

CA $464 total

includes taxes & fees

Sep 21 - Sep 22

3. Storm King Lodge - Storm King Art Center, West Point, Woodbury Commons Outlets

Mountainville

Robert D.

CA $1,609

CA $2,204 total

includes taxes & fees

Sep 20 - Sep 21

View all properties

Top Chester Hotel Reviews

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

8/10 Good

"Clean room everything works"

Inn on the Hudson

8/10 Good

"The location is quiet and peaceful. The room o the other hand is outdated and dusty."

Overlook Lodge at Bear Mountain

8/10 Good

"It is a very nice place .To bad the pool was not open ."

The Thayer Hotel at West Point

10/10 Excellent

"Lovely place with a great restaurant and dining room!!"

Hampton Inn & Suites Mahwah

10/10 Excellent

"Everything was nice and smelled good. It was also very quiet. The bed wasn’t super comfortable but that was probably just Me. The staff was always smiling."

Sonesta Simply Suites Nanuet

10/10 Excellent

"The staff was the best part: very friendly and helpful. The room was newly renovated, and although there was some mild, but normal, construction noise during the day (9AM-5PM, or thereabouts), it was done during normal resting hours. There was a 24 hour gym/laundry room that were connected. The gym had dumbbells on a rack, which is good, and a universal-type weight machines. Some of the equipment could have used updating, but it was better than nothing. I couldn’t find the remote- or figure out how to turn the tv on. I was using it at around 11:30 PM. I didn’t look closely enough to see about breakfast, I just jumped on the hotel for convenience of location. I missed the fact there was no breakfast -and spent a bit more time looking for a good breakfast than I would have liked. The traffic patterns in the area are VERY weird, and it’s REALLY EASY to miss turns, but that’s obviously not the hotel’s fault. Ashley and General Manager Rickie were very helpful and friendly! The suites have kitchens, but when I go to hotels, I don’t want to cook! The parking lot had just enough spaces - many were taken up by construction trailers & equipment. Overall- a good place to stay, but I usually prefer a place where I can walk to get some breakfast."

Holiday Inn Express Ramsey-Mahwah by IHG

10/10 Excellent

"very hospitable"

Hilton Garden Inn Nanuet

10/10 Excellent

"Property is old and could use a redo. But the property is well maintained. Rooms were clean and comfortable."

Ramada by Wyndham Newburgh/West Point

10/10 Excellent

"Non"

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 21 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. Additionally, you'll find Woodbury Common Premium Outlets in the area.

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.

Explore a world of travel with Expedia

Book Historic Hotels in Chester on Expedia.com

Find Historic Hotels in Chester, NY from CA $187

Change your mind

Treat yourself

Be picky

Check availability on Chester Historic Hotels

Our top choices for Chester historic hotels

1. Overlook Lodge at Bear Mountain

2. Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

3. Storm King Lodge - Storm King Art Center, West Point, Woodbury Commons Outlets

Top Chester Hotel Reviews

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Inn on the Hudson

Overlook Lodge at Bear Mountain

The Thayer Hotel at West Point

Hampton Inn & Suites Mahwah

Sonesta Simply Suites Nanuet

Holiday Inn Express Ramsey-Mahwah by IHG

Hilton Garden Inn Nanuet

Ramada by Wyndham Newburgh/West Point

Frequently asked questions

Explore a world of travel with Expedia