Photo by William E Berry Jr.

Find Historic Hotels in Windsor, VT

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Check availability on Windsor Historic Hotels

Tonight
3 Oct - 4 Oct
Tomorrow
4 Oct - 5 Oct
This weekend
3 Oct - 5 Oct
Next weekend
10 Oct - 12 Oct

Top Windsor Historic Hotels

Hotel Coolidge
Interior

Hotel Coolidge

3.0 star property
8.2 out of 10, Very Good, (1007)
"Loved the look of the historical hotel."
Hotel Coolidge
Hanover Inn Dartmouth
Breakfast, lunch, dinner served; local cuisine

Hanover Inn Dartmouth

4.0 star property
9.6 out of 10, Exceptional, (872)
"Perfect hotel "
The price is AED 1,322
AED 1,435 total
includes taxes & fees
14 Oct - 15 Oct
Hanover Inn Dartmouth
Cedarbrook Hotel Room 2 Doubles 119
Interior

Cedarbrook Hotel Room 2 Doubles 119

9.0 out of 10, Wonderful, (7)
"The place was an ok place to "crash" after a day of out side activities. The rug needs to be replaced or shampooed. The beds are not very comfortable. "
The price is AED 420
AED 623 total
includes taxes & fees
6 Oct - 7 Oct
Cedarbrook Hotel Room 2 Doubles 119
Beautiful home offering privacy on 7 acres with private pond
Interior

Beautiful home offering privacy on 7 acres with private pond

10.0 out of 10, Exceptional, (30)
"Very relaxing house, we all enjoyed the fireplaces and pellet stove and the well-equipped kitchen allowed us to cook beautiful meals. The property is gorgeous and neighbors are far away. This was the perfect place for a friends reunion/ski trip!"
The price is AED 843
AED 1,911 total
includes taxes & fees
8 Oct - 9 Oct
Beautiful home offering privacy on 7 acres with private pond
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Exterior

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

9.6 out of 10, Exceptional, (163)
"We very much enjoyed our stay, check in was a breeze and we found the cabin to be a cozy retreat. We have been looking for a place that had a bed and bath on first floor to accommodate some mobility limitations and this home was perfect having a single step on the front porch. We look forward to booking another trip with this host "
The price is AED 624
AED 1,358 total
includes taxes & fees
6 Oct - 7 Oct
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Microwave, oven, stovetop, dishwasher

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

10.0 out of 10, Exceptional, (98)
"Wonderful two bedroom condo, fantastic communication from the manager, easy everything, parking, accessing the beautiful unit, checking out, just perfect!"
The price is AED 544
AED 1,104 total
includes taxes & fees
28 Oct - 29 Oct
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Fridge, microwave, oven, stovetop

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

9.8 out of 10, Exceptional, (103)
"Great location and house was very nice."
The price is AED 768
AED 1,539 total
includes taxes & fees
28 Oct - 29 Oct
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
TV, DVD player

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

9.4 out of 10, Exceptional, (24)
"Very nice accommodations"
The price is AED 198
AED 809 total
includes taxes & fees
7 Oct - 8 Oct
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Ski-in/out condo near ski school with washer/dryer, fast WiFi, & mountain views
Interior

Ski-in/out condo near ski school with washer/dryer, fast WiFi, & mountain views

7.4 out of 10, Good, (13)
"It ain’t the Ritz but the location and accessibility to the mountain is what you are paying for (and what you want.) Very functional, very efficient, and very convenient ski condo. Highly recommended. "
The price is AED 823
AED 1,561 total
includes taxes & fees
31 Oct - 1 Nov
Ski-in/out condo near ski school with washer/dryer, fast WiFi, & mountain views
Queen Studio on the 2nd floor with outdoor heated pool 207
Interior

Queen Studio on the 2nd floor with outdoor heated pool 207

8.0 out of 10, Very Good, (6)
"Overall a good option for a visit to Killington if you don’t need to be on the access road. The outdoor heated pool was a really nice way to relax after a day of skiing. If you don’t want to drive, there is a pretty good restaurant across the street. The only slight concern is if more units than unit 207 are listed on VRBO (the unit we stayed in). I’m glad we had an upstairs unit because the floor was very squeaky. I was wondering if it was annoying the unit below us. With that minor detail...
The price is AED 420
AED 623 total
includes taxes & fees
19 Oct - 20 Oct
Queen Studio on the 2nd floor with outdoor heated pool 207
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.
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Top Windsor Hotel Reviews

Hotel Coolidge

Hotel Coolidge

10/10 Excellent
"Very nice well maintained historical property. Very friendly,courteous, and efficient staff. "
LEVAREL 1-night trip
Posted 3 days ago
Hotel Coolidge

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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 20 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. Natural beauty is on display at Connecticut River, Path of Life Garden, and Paradise Park. 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.