Find Historic Hotels in Chester, VT from CA $179

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Our top choices for Chester historic hotels

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 reviews)
"Beautiful cozy cottage. Very clean. Wonderful host."
United States
Gloria A.
The price is CA $324
CA $401 total
includes taxes & fees
May 3 - May 4
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

Entire Farmhouse with lots of open space 15 min north of Keene
Walpole
10.0 out of 10, Exceptional, (38 reviews)
"Lovely place would definitely book again"
United States
Sean M.
The price is CA $409
CA $505 total
includes taxes & fees
May 3 - May 4
Entire Farmhouse with lots of open space 15 min north of Keene

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, (169 reviews)
"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 CA $233
CA $503 total
includes taxes & fees
May 7 - May 8
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Castle Hill Resort And Spa

Castle Hill Resort And Spa
3.5 star property
Cavendish
9.0 out of 10, Wonderful, (118 reviews)
"This was our second time staying here and it never disappoints! I booked this trip during our kids' spring break for a quick getaway and to use the amazing heated outdoor pool. It's a great location convenient to all the amazing sites Vermont has to offer. Would love to go back again in the fall!"
United States
Jennifer
The price is CA $235
CA $256 total
includes taxes & fees
May 6 - May 7
Castle Hill Resort And Spa

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, (108 reviews)
"We enjoyed our stay, the house was lovely and close to everything in Ludlow and Okemo."
United States
Hannah M.
The price is CA $171
CA $442 total
includes taxes & fees
May 6 - May 7
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

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Clock Tower Base Area
9.2 out of 10, Wonderful, (30 reviews)
"Great property, clean and close to the slope"
United States
tiliger01
The price is CA $67
CA $302 total
includes taxes & fees
May 2 - May 3
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

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
9.8 out of 10, Exceptional, (109 reviews)
"Convenient 2 BR space with comfy beds right in the heart of Ludlow. Would definitely stay there again."
United States
Andrew L.
The price is CA $186
CA $390 total
includes taxes & fees
May 3 - May 4
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck

Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck
Plymouth
9.8 out of 10, Exceptional, (24 reviews)
"The Nest at Hawk Ledges was a perfect summer getaway. The home provides comfort in a tranquil setting while being close enough to many summer adventures. We enjoyed relaxing in the bright, open home after taking many day trips to explore the area. What a gem!"
United States
Ben N.
The price is CA $267
CA $973 total
includes taxes & fees
May 19 - May 20
Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck

Two Double bed Hotel Room with outdoor heated pool 216

Two Double bed Hotel Room with outdoor heated pool 216
Killington
The price is CA $112
CA $179 total
includes taxes & fees
May 2 - May 3
Two Double bed Hotel Room with outdoor heated pool 216

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, (7 reviews)
"Efficient and affordable option for a short stay."
United States
Marnie O.
The price is CA $112
CA $179 total
includes taxes & fees
May 1 - May 2
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.

Top Chester Hotel Reviews

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 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 North Springfield Lake Recreation Area 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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