A covered wooden bridge over a river, surrounded by rocky terrain and greenery.

Find Historic Hotels in Chester, VT from CA $344

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Check availability on Chester Historic Hotels

Tonight
Oct 17 - Oct 18
Tomorrow
Oct 18 - Oct 19
Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1

Our top choices for Chester historic hotels

A large stone building with a steep roof, surrounded by dense forest and hills.
A hotel room with a bed, a nightstand, a lamp, a door, and a view into another room with a couch and a window.
A traditional bedroom with a four-poster bed, two armchairs, a wooden wardrobe, and a mirror.
A spacious living room with a fireplace, comfortable seating, and a large window providing natural light.

1. Castle Hill Resort And Spa

Castle Hill Resort And Spa
Cavendish
United States
Brandon
CA $316
CA $344 total
includes taxes & fees
Oct 27 - Oct 28
Castle Hill Resort And Spa
A red house with a covered porch and a chimney.
A kitchen with a wooden table and chairs, a microwave, and cabinets.
Two single beds with wooden frames and striped bedding, a small wooden nightstand with a lamp, and a window with a view of greenery.
A living room with a wood-burning stove, a blue armchair, and a bookshelf.

2. Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
United States
Eleanor D.
CA $240
CA $526 total
includes taxes & fees
Oct 20 - Oct 21
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
A cozy living room with a fireplace, a black leather sofa, and a television mounted above it.
A bedroom with a bed, a nightstand, a lamp, a painting of a snowy forest, and a window with curtains.
A modern living room with a black leather sofa, wooden flooring, and exposed wooden beams on the ceiling.
A golf course with a clubhouse, surrounded by lush greenery and hills.

3. 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
United States
Justin P.
CA $239
CA $563 total
includes taxes & fees
Nov 17 - Nov 18
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.
A living room with a flat-screen TV, a sofa, a coffee table, and a lamp.
A compact kitchen with white cabinets, a dishwasher, and a countertop with various appliances.
A two-story house with a porch, a white picket fence, and a tree in front.

4. 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
United States
Tina l.
CA $328
CA $734 total
includes taxes & fees
Nov 15 - Nov 16
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
View all properties

Top Chester Hotel Reviews

Colonial Motel

Colonial Motel

10/10 Excellent
"Value for money. Clean and conveniently located. Friendly staff."
Swaraj 2-night trip
Posted 20 hours ago
Colonial Motel
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

8/10 Good
"Ij kii it"
Kevin 2-night trip
Posted 1 day ago
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
The Manchester View

The Manchester View

10/10 Excellent
"Staff was so sweet and accommodating and we really enjoyed the delicious breakfast in the morning. We will definitely return!"
Janee 1-night trip
Posted 3 days ago
The Manchester View
Aspen At Manchester

Aspen At Manchester

10/10 Excellent
"Great location, simple room--minimalist but nice with microwave, fridge. Was a great place to set up headquarters for our trip to Vermont. Beautiful view behind the motel with firepits. It is a self-serve kind of property, which suited us well. We stayed 4 days and they didn't come to clean throughout. But we could go to the office and pick up anything we needed: extra toiletries, towels, etc. We enjoyed staying at the Aspen."
Sarah 4-night trip
Posted 3 days ago
Aspen At Manchester
The Equinox Golf Resort And Spa

The Equinox Golf Resort And Spa

10/10 Excellent
"Good"
Kenton 2-night trip
Posted 4 days ago
The Equinox Golf Resort And Spa
On The River Inn

On The River Inn

10/10 Excellent
"Karen at the front desk was absolutely delightful. She saw me struggling with my dog and bags, and helped me to my room. Dan on the housekeeping was so nice. We saw him almost every day. The hotel is incredibly pet friendly. It's so convenient to walk out of your room directly onto the rear lawn, and down toward the river. I had a nice chat with the lady who lives across the river. She also has a dog. The drive to downtown was just a few minutes. I highly recommend the farmer's market (you pass it on the way to downtown Woodstock). The room was very clean. The sink and bathroom door could use some updates, but other than that it was lovely. I would definitely return again with my pup."
VS 4-night trip
Posted 11 days ago
On The River Inn

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 relaxing 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 67 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 Country Store and Lowell Lake State Park 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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