Find Historic Hotels in Windsor, VT

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Top Windsor Historic Hotels

Interior
Beautiful home offering privacy on 7 acres with private pond

Beautiful home offering privacy on 7 acres with private pond

West Windsor
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!"
United States
Roy S.
The price is AED 777
AED 1,824 total
includes taxes & fees
20 Nov - 21 Nov
Beautiful home offering privacy on 7 acres with private pond
Interior
Hotel Coolidge

Hotel Coolidge

3.0 star property
White River Junction
8.2 out of 10, Very Good, (1001)
"The off street parking was good, the staff was great. "
United States
Sheryl
Hotel Coolidge
Interior
Cedarbrook Hotel Room 2 Doubles 119

Cedarbrook Hotel Room 2 Doubles 119

Killington
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. "
United States
Leslie
The price is AED 465
AED 680 total
includes taxes & fees
20 Nov - 21 Nov
Cedarbrook Hotel Room 2 Doubles 119
Full-size fridge, microwave, oven, stovetop
Deluxe One bedroom Queen Suite on the 2nd floor with outdoor heated pool 209

Deluxe One bedroom Queen Suite on the 2nd floor with outdoor heated pool 209

Killington
9.0 out of 10, Wonderful, (13)
"Our experience was easy and relaxing. It was nice and close to Killington Mountain and everything that we needed for the weekend was available."
United States
Parker D.
The price is AED 667
AED 958 total
includes taxes & fees
20 Nov - 21 Nov
Deluxe One bedroom Queen Suite on the 2nd floor with outdoor heated pool 209
Exterior
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, (166)
"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 AED 624
AED 1,358 total
includes taxes & fees
1 Dec - 2 Dec
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Microwave, oven, stovetop, dishwasher
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
10.0 out of 10, Exceptional, (102)
"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 AED 511
AED 1,063 total
includes taxes & fees
20 Nov - 21 Nov
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Fridge, microwave, oven, stovetop
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, (103)
"A lovely time enjoying the off-season in a ski town. "
United States
Ed C.
The price is AED 834
AED 1,660 total
includes taxes & fees
20 Nov - 21 Nov
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
TV, DVD player
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, (25)
"Loved the location"
United States
Steven W.
The price is AED 246
AED 891 total
includes taxes & fees
2 Dec - 3 Dec
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Interior
Queen Studio on the 2nd floor with outdoor heated pool 207

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

Killington
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...
United States
John S.
The price is AED 465
AED 684 total
includes taxes & fees
1 Dec - 2 Dec
Queen Studio on the 2nd floor with outdoor heated pool 207
TV, books, offices
Two Queen Bed Standard Hotel room with outdoor heated pool 201

Two Queen Bed Standard Hotel room with outdoor heated pool 201

Killington
8.8 out of 10, Excellent, (13)
"It was a great place for us to spend the night before continuing our travel up north to see the eclipse ☀️ "
United States
Lucy Marshall
The price is AED 465
AED 685 total
includes taxes & fees
20 Nov - 21 Nov
Two Queen Bed Standard Hotel room with outdoor heated pool 201
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
"Easy check-in, friendly staff, old-timey New England atmosphere, free coffee in lobby 24/7 to guests with fire place "
Anne 1-night trip
Posted 1 day 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 23 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.