Find Historic Hotels in Chester, VT

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Nov 26 - Nov 27
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Dec 5 - Dec 7

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)
"Excellent place!!!! Lovely room that had all I needed!!! The bed was comfortable and the stay was wonderful!!!!!!"
United States
natalia
$183 nightly
The price is $198
Nov 30 - Dec 1
Total with taxes and fees
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)
"Beautiful cozy cottage. Very clean. Wonderful host."
United States
Gloria A.
$231 nightly
The price is $250
Dec 1 - Dec 2
Total with taxes and fees
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)
"Lovely place would definitely book again"
United States
Sean M.
$270 nightly
The price is $293
Dec 1 - Dec 2
Total with taxes and fees
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
$327 nightly
The price is $366
Dec 15 - Dec 16
Total with taxes and fees
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
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)
"Convenient 2 BR space with comfy beds right in the heart of Ludlow. Would definitely stay there again."
United States
Andrew L.
$280 nightly
The price is $304
Dec 1 - Dec 2
Total with taxes and fees
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.
$408 nightly
The price is $443
Dec 1 - Dec 2
Total with taxes and fees
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)
"Loved the location"
United States
Steven W.
$217 nightly
The price is $245
Dec 8 - Dec 9
Total with taxes and fees
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Interior
Two Double bed Hotel Room with outdoor heated pool 216

Two Double bed Hotel Room with outdoor heated pool 216

Killington
$170 nightly
The price is $185
Nov 30 - Dec 1
Total with taxes and fees
Two Double bed Hotel Room with outdoor heated pool 216
Interior
Queen Studio on the 2nd floor with outdoor heated pool 207

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

Killington
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...
United States
John S.
$171 nightly
The price is $186
Nov 30 - Dec 1
Total with taxes and fees
Queen Studio on the 2nd floor with outdoor heated pool 207
Interior
Cedarbrook Hotel Room 2 Doubles 119

Cedarbrook Hotel Room 2 Doubles 119

Killington
9.0 out of 10, Wonderful, (7)
"The place was an ok place to "crash" after a day of out side activities. The rug needs to be replaced or shampooed. The beds are not very comfortable. "
United States
Leslie
$170 nightly
The price is $185
Nov 30 - Dec 1
Total with taxes and fees
Cedarbrook Hotel Room 2 Doubles 119
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 Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

10/10 Excellent
"Courteous staff Clean room"
Laura 1-night trip
Posted 5 days ago
The Equinox Golf Resort & Spa

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. Phineas Gage Memorial is a short 16-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 DaVallia Art & Accents and Bonnie's Bundles Dolls. 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.

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