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

Find Historic Hotels in Windsor, VT from CA $342

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Check availability on Windsor Historic Hotels

Tonight
Oct 15 - Oct 16
Tomorrow
Oct 16 - Oct 17
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

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, red sofas, a wooden coffee table, and a television.
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 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 $314
CA $342 total
includes taxes & fees
Oct 22 - Oct 23
Castle Hill Resort And Spa
A hotel lobby with a fireplace, seating areas, and large arched windows.
A conference room with a fireplace, large windows, and a view of the outdoors.
A brick building with a covered entrance labeled 'HANOVER INN.'
A spacious living room with a high ceiling, a fireplace, and a large dining table.

2. Hanover Inn Dartmouth

Hanover Inn Dartmouth
Hanover
United States
Laly
CA $391
CA $424 total
includes taxes & fees
Nov 15 - Nov 16
Hanover Inn Dartmouth
A red house with a covered porch and a chimney.
A kitchen with a wooden table and chairs, a microwave, and cabinets.
A kitchen with white cabinets, a microwave, a stove, and a sink.
Two single beds with wooden frames and striped bedding, a small wooden nightstand with a lamp, and a window with a view of greenery.

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 $242
CA $521 total
includes taxes & fees
Nov 4 - Nov 5
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
View all properties

Top Windsor Hotel Reviews

Align Inn Vermont

Align Inn Vermont

10/10 Excellent
"The room was great as well as the breakfast, we enjoyed our stay and would stay again."
Gary 1-night trip
Posted 10 hours ago
Align Inn Vermont
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

10/10 Excellent
"My sister and I needed a very last minute place to stay after our VRBO rental was not what we thought. The ladies at the front desk were really nice and very help. The beds and pillows were very comfortable and the room was very clean. The only issue is the area, it’s a bit of a drive if you want to shop however, one minute up the road is Murdoch’s restaurant and they had delicious food. We ate there twice. Just make sure to make a reservation. All in all it was a nice stay and we definitely suggest staying there."
Stephanie 1-night trip
Posted 2 days ago
Pointe at Castle Hill Resort
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 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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