A snow-covered river valley with a bridge and a town.

Find Historic Hotels in Windsor, VT from CA $336

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Check availability on Windsor Historic Hotels

Tonight
Sep 27 - Sep 28
Tomorrow
Sep 28 - Sep 29
Next weekend
Oct 2 - Oct 4
In two weeks
Oct 9 - Oct 11

Our top choices for Windsor historic hotels

A large stone building with a steep roof, surrounded by dense forest and hills.
A spacious living room with a fireplace, comfortable seating, and a large window providing natural light.
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.

1. Castle Hill Resort And Spa

Castle Hill Resort And Spa
Cavendish
United States
Brandon
CA $308
CA $336 total
includes taxes & fees
Oct 28 - Oct 29
Castle Hill Resort And Spa
A hotel lobby with a fireplace, seating areas, and large arched windows.
A spacious living room with a high ceiling, a fireplace, and a large dining table.
A conference room with a fireplace, large windows, and a view of the outdoors.
A conference room with a fireplace, large windows, and a view of the outdoors.

2. Hanover Inn Dartmouth

Hanover Inn Dartmouth
Hanover
United States
Laly
CA $467
CA $507 total
includes taxes & fees
Sep 29 - Sep 30
Hanover Inn Dartmouth
A red house with a covered porch and a chimney.
A kitchen with white cabinets, a microwave, a stove, and a sink.
A kitchen with a wooden table and chairs, a microwave, and cabinets.
A living room with a wood-burning stove, a blue armchair, and a bookshelf.

3. 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 $516 total
includes taxes & fees
Sep 30 - Oct 1
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
View all properties

Top Windsor Hotel Reviews

The Jackson

The Jackson

10/10 Excellent
"Garden and grounds out back were very nice. Restaurant provided great dinner and breakfast."
Rick 2-night trip
Posted 2 hours ago
The Jackson
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

10/10 Excellent
"The Dalmatian behind the front desk"
April 2-night trip
Posted 1 day ago
Pointe at Castle Hill Resort
Hotel Coolidge

Hotel Coolidge

8/10 Good
"We loved the coffee in the lobby and dinner recommendations. Comfortable room."
Sharon 1-night trip
Posted 6 days ago
Hotel Coolidge
On The River Inn

On The River Inn

8/10 Good
"Extremely quaint and love the rooms and balcony… Dining room gorgeous Wish there were Apps on the Tv for streaming… that’s all"
Marcia 2-night trip
Posted 9 days ago
On The River Inn

Frequently asked questions

What should I expect on my historical trip to Windsor?
The historical sites in Windsor are probably at the top of your sightseeing list. You can also discover all there is to see and do such as the breweries and golf courses
How many historical hotels are there in Windsor?
In Windsor, there are 21 hotels and other accommodations bookable on Expedia though not many historic hotels to choose from.
What are the most important historical places and other sights to visit in Windsor?
Windsor is notable for landmarks like Old Constitution House. The picturesque setting of Connecticut River and Paradise Park exemplify the area's natural beauty. A couple of additional sights to add to your agenda are American Precision Museum and Harpoon Brewery.
What is a historic hotel like in Windsor?
When you book a historic hotel, you'll stay someplace that has a national historic designation. A palace, castle, stately home or even a lodge, pub, or skyscraper can be identified as a historic hotel as long as it's of special interest. Traditional architecture and period features are often preserved in the public spaces and guestrooms of historic hotels in Windsor, giving a historical feel.
What is the difference between a historic hotel and a heritage hotel?
"Heritage hotel" is a term often used in Asia and Europe, while "historic hotel" is a term often used in the U.S. though overall the terms are quite similar. The physical building and architecture of historic hotels tend to be the most significant aspect. For a heritage hotel, it's mainly the cultural value as well as how it influenced the community.
Do historic hotels in Windsor have modern facilities?
Hotel interiors feature the modern conveniences and safety features you expect to find, but every effort is made to preserve historic facades and treasured traditions. Private rooms with updated bathroom facilities, heating and air conditioning, free and fast Internet, and the usual amenities found in any hotel should be available at a historic hotel. When you choose a historic hotel in Windsor, don't worry that you'll find yourself staying at a place that's uncomfortable or rundown.

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