Find Historic Hotels in Chester, VT

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Check availability on Chester Historic Hotels

Tonight
1 Oct - 2 Oct
Tomorrow
2 Oct - 3 Oct
This weekend
3 Oct - 5 Oct
Next weekend
10 Oct - 12 Oct

Top Chester Historic Hotels

The Carriage Barn Inn
Free daily continental breakfast

The Carriage Barn Inn

3.0 star property
9.6 out of 10, Exceptional, (156)
"Very quiet and peaceful but at the same time it's right down the street from Main Street. Joe the owner was so nice! "
The price is AED 697
AED 757 total
includes taxes & fees
9 Oct - 10 Oct
The Carriage Barn Inn
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
TV, books

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

10.0 out of 10, Exceptional, (8)
"Great, clean, charming cottage. The hosts are amazing and communicated every detail, very hospitable. Highly recommend. "
The price is AED 878
AED 1,076 total
includes taxes & fees
27 Oct - 28 Oct
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Entire Farmhouse with lots of open space 15 min north of Keene
Exterior detail

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

10.0 out of 10, Exceptional, (37)
"Great location, great house, and wonderful breakfast. Would highly recommend and plan to stay there again some day soon."
The price is AED 1,025
AED 1,255 total
includes taxes & fees
27 Oct - 28 Oct
Entire Farmhouse with lots of open space 15 min north of Keene
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Exterior

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

9.6 out of 10, Exceptional, (162)
"We very much enjoyed our stay, check in was a breeze and we found the cabin to be a cozy retreat. We have been looking for a place that had a bed and bath on first floor to accommodate some mobility limitations and this home was perfect having a single step on the front porch. We look forward to booking another trip with this host "
The price is AED 624
AED 1,358 total
includes taxes & fees
6 Oct - 7 Oct
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Microwave, oven, stovetop, dishwasher

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

10.0 out of 10, Exceptional, (98)
"Wonderful two bedroom condo, fantastic communication from the manager, easy everything, parking, accessing the beautiful unit, checking out, just perfect!"
The price is AED 536
AED 1,092 total
includes taxes & fees
29 Oct - 30 Oct
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (103)
"Great location and house was very nice."
The price is AED 779
AED 1,552 total
includes taxes & fees
28 Oct - 29 Oct
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
TV, DVD player

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

9.4 out of 10, Exceptional, (24)
"Very nice accommodations"
The price is AED 253
AED 882 total
includes taxes & fees
7 Oct - 8 Oct
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Queen Studio on the 2nd floor with outdoor heated pool 207
Interior

Queen Studio on the 2nd floor with outdoor heated pool 207

8.0 out of 10, Very Good, (6)
"Overall a good option for a visit to Killington if you don’t need to be on the access road. The outdoor heated pool was a really nice way to relax after a day of skiing. If you don’t want to drive, there is a pretty good restaurant across the street. The only slight concern is if more units than unit 207 are listed on VRBO (the unit we stayed in). I’m glad we had an upstairs unit because the floor was very squeaky. I was wondering if it was annoying the unit below us. With that minor detail...
The price is AED 420
AED 623 total
includes taxes & fees
19 Oct - 20 Oct
Queen Studio on the 2nd floor with outdoor heated pool 207
Two Queen Bed Standard Hotel room with outdoor heated pool 201
TV, books, offices

Two Queen Bed Standard Hotel room with outdoor heated pool 201

8.6 out of 10, Excellent, (12)
"Our room was easy to find and very clean. And the late check-in was very helpful."
The price is AED 420
AED 624 total
includes taxes & fees
29 Oct - 30 Oct
Two Queen Bed Standard Hotel room with outdoor heated pool 201
107 Deluxe Studio Queen, w/ Sleeper sofa w/ outdoor heated pool
Exterior

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

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"
The price is AED 420
AED 623 total
includes taxes & fees
14 Oct - 15 Oct
107 Deluxe Studio Queen, w/ Sleeper sofa w/ outdoor heated pool
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

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent
"Very clean, up to date, affordable"
Daniel 1-night trip
Posted 1 day ago
Keene Elm City Hotel, an Ascend Collection Hotel

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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 66 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 DaVallia Art & Accents and Bonnie's Bundles Dolls. You'll also find Vermont Museum of Mining and Minerals and Vermont Country Store 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.