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

Find Historic Hotels in Windsor, VT from CA $288

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Check availability on Windsor Historic Hotels

Tonight
Sep 17 - Sep 18
Tomorrow
Sep 18 - Sep 19
This weekend
Sep 18 - Sep 20
Next weekend
Sep 25 - Sep 27

Our top choices for Windsor historic hotels

Front of property
Flat-screen TV
Condo Hotel Room
Standard Room, 1 Queen Bed

1. Castle Hill Resort And Spa

Castle Hill Resort And Spa
Cavendish
United States
Mirco
CA $264
CA $288 total
includes taxes & fees
Oct 18 - Oct 19
Castle Hill Resort And Spa
Breakfast, lunch, dinner and brunch served
Exterior
Lobby
Meeting facility

2. Hanover Inn Dartmouth

Hanover Inn Dartmouth
Hanover
United States
Laly
CA $434
CA $471 total
includes taxes & fees
Sep 20 - Sep 21
Hanover Inn Dartmouth
Exterior
Dining
Interior
2 bedrooms, iron/ironing board, WiFi (free), bed sheets

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 $237
CA $514 total
includes taxes & fees
Sep 22 - Sep 23
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
View all properties

Top Windsor Hotel Reviews

On The River Inn

On The River Inn

8/10 Good
"Housekeeping was a bit lax. No tissues and only one hand towel. The rest of the Inn was great!"
Marion 1-night trip
Posted 14 hours ago
On The River Inn
The Jackson

The Jackson

10/10 Excellent
"Close enough to Woodstock yet far enough away to be peaceful. Very kind staff."
joanne 1-night trip
Posted 20 hours ago
The Jackson
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

10/10 Excellent
"I loved that they have 2 room suites with a full kitchen. Everyone who worked there was beyond efficient and friendly. The fact that its dog friendly was great as I had been on the road almost 3 weeks and was missing my pups ."
Linda 3-night trip
Posted 1 day ago
Pointe at Castle Hill Resort
Hotel Coolidge

Hotel Coolidge

10/10 Excellent
"Great historic hotel with nice and helpful staff in the middle of town."
Elizabeth 3-night trip
Posted 4 days ago
Hotel Coolidge

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 Harpoon Brewery and Mt Ascutney State Park.
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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