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Check availability on Chester Historic Hotels

Top Chester Historic Hotels

Free daily continental breakfast
The Carriage Barn Inn

The Carriage Barn Inn

3.0 star property
Keene
9.6 out of 10, Exceptional, (165)
"This BNB is delightful. Great location and easy to find in town. Lovely house, room, easy check in, and the owner was great. The owner was there when we checked in and gave us a tour and recommendations for dinner in town. Downtown is just darling and easy walking around the town square. Dinner in town was excellent as well. I would highly recommend a stay here to anyone. "
United States
Tina
The price is AED 604
AED 655 total
includes taxes & fees
1 Dec - 2 Dec
The Carriage Barn Inn
TV, books
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Walpole
10.0 out of 10, Exceptional, (8)
"Easy hand's off check in and great communication with the host. The cottage itself was lovely - my friends and I were in town for a wedding and it was the perfect accommodations! Would definitely stay here again! "
United States
Frances D.
The price is AED 752
AED 919 total
includes taxes & fees
17 Nov - 18 Nov
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Exterior detail
Entire Farmhouse with lots of open space 15 min north of Keene

Entire Farmhouse with lots of open space 15 min north of Keene

Walpole
10.0 out of 10, Exceptional, (38)
"Great location, great house, and wonderful breakfast. Would highly recommend and plan to stay there again some day soon."
United States
Evan T.
The price is AED 877
AED 1,075 total
includes taxes & fees
17 Nov - 18 Nov
Entire Farmhouse with lots of open space 15 min north of Keene
Exterior
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Grafton
9.6 out of 10, Exceptional, (166)
"Very nice and clean cabin, not too far from small towns, decently supplied for expected conveniences, charming area - a small stream nearby provides a pleasant background noise. "
United States
Philip
The price is AED 624
AED 1,312 total
includes taxes & fees
17 Nov - 18 Nov
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Interior
Beautiful home offering privacy on 7 acres with private pond

Beautiful home offering privacy on 7 acres with private pond

West Windsor
10.0 out of 10, Exceptional, (30)
"Lots of space inside and out for my family to enjoy here! The sunny living room with its many windows brings the outside indoors."
United States
Eileen W.
The price is AED 747
AED 1,787 total
includes taxes & fees
18 Nov - 19 Nov
Beautiful home offering privacy on 7 acres with private pond
Microwave, oven, stovetop, dishwasher
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

Ludlow
10.0 out of 10, Exceptional, (102)
"Pretty nice little condo in a nice location."
United States
jonathan H.
The price is AED 485
AED 1,025 total
includes taxes & fees
17 Nov - 18 Nov
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Fridge, microwave, oven, stovetop
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Ludlow
9.8 out of 10, Exceptional, (103)
"A lovely time enjoying the off-season in a ski town. "
United States
Ed C.
The price is AED 738
AED 1,535 total
includes taxes & fees
17 Nov - 18 Nov
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
TV, DVD player
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Clock Tower Base Area
9.2 out of 10, Wonderful, (25)
"My sister and our two sons stayed here. It was simple, and extraordinarily convenient . It could use some updating - namely the pull out sofa mattress - labeled from 1992. Not comfortable. Besides that, it was right for the price if convenience is a priority."
United States
Justin B.
The price is AED 239
AED 882 total
includes taxes & fees
20 Nov - 21 Nov
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Exterior
107 Deluxe Studio Queen, w/ Sleeper sofa w/ outdoor heated pool

107 Deluxe Studio Queen, w/ Sleeper sofa w/ outdoor heated pool

Killington
8.0 out of 10, Very Good, (6)
"The check in process was so easy, our room was clean and had everything we needed. We would definitely stay here again"
United States
Lindsey W.
The price is AED 465
AED 684 total
includes taxes & fees
17 Nov - 18 Nov
107 Deluxe Studio Queen, w/ Sleeper sofa w/ outdoor heated pool
Interior
Two Queen Bed Standard Hotel Room w/outdoor heated pool 204

Two Queen Bed Standard Hotel Room w/outdoor heated pool 204

Killington
8.4 out of 10, Very Good, (18)
"The staff was very nice. The room was clean. The only complaint we would have is to let the people who are in the room we had know that the water pump is very loud. Every time someone used water the pump kicked on and it was loud. Other than that very nice place and we would highly recommend. "
United States
Jonathan and Deborah
The price is AED 465
AED 685 total
includes taxes & fees
17 Nov - 18 Nov
Two Queen Bed Standard Hotel Room w/outdoor heated pool 204
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

The Jackson

The Jackson

10/10 Excellent
"The room, the staff, the amenities were what we were hoping for. The Jackson is a great place to stay! "
Frederick 2-night trip
Posted 2 days ago
The Jackson

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Frequently asked questions

What should I expect on my historical trip to Chester?
A trip to the sights with historical relevance in Chester is probably at the top of your sightseeing list. Visit the ski slopes and shops while you're in town. During your stay in this quaint area, you can also relish a trip to the coffeehouses.
What's the best place to stay in Chester that's close to historical sites?
Based on our travel expertise, 1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO! is a top guesthouse for history seekers booking on Expedia, and it features free WiFi and laundry facilities. Baltimore Covered Bridge is a short 17-minute drive away.
How many historical hotels are there in Chester?
In Chester, there are 68 hotels and other lodging options bookable on Expedia but not many designated as historic hotels.
What are the must-see historical sites and other places to visit in Chester?
A couple of favorite places to visit are Bonnie's Bundles Dolls and DaVallia Art & Accents. Additionally, you'll find Stratton Mountain Resort in the area.
What is a historic hotel like in Chester?
By choosing a historic hotel, you can spend a night or two in a building that has an officially recognized historic designation. A palace, castle, stately home or even a lodge, pub, or skyscraper can be turned into a historic hotel as long as it's a place of special interest. Traditional architecture and period features are typically found in the guestrooms or communal spaces of such hotels in Chester, giving a real sense of character.
What is the difference between a historic hotel and a heritage hotel?
"Heritage hotel" is more common in Asia and Europe, while "historic hotel" is more common in the U.S. overall though the terms are similar. The architecture and actual building of a historic hotel is generally what's most important. For a heritage hotel, often it's the cultural value along with how it influenced the community.
Do historic hotels in Chester have modern facilities?
Hotel interiors feature the modern conveniences and safety features you expect to find, while every effort is made to preserve historic facades and treasured traditions. WiFi, heating and air conditioning, updated bathroom facilities, and the amenities found in any hotel should be available at a historic hotel. Rest assured that when you choose a historic hotel in Chester, you won't find yourself staying at a place that is rundown or uncomfortable.