Find Historic Hotels in Windsor, VT

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Check availability on Windsor Historic Hotels

Tonight
27 Feb - 28 Feb
Tomorrow
28 Feb - 1 Mar
This weekend
27 Feb - 1 Mar
Next weekend
6 Mar - 8 Mar

Our top choices for Windsor historic hotels

Breakfast, lunch, dinner served; local cuisine

Hanover Inn Dartmouth

Hanover Inn Dartmouth
4.0 star property
Hanover
9.6 out of 10, Exceptional, (918 reviews)
"Friendly. Clean, good location"
United States
Deborah
The price is AED 834
AED 905 total
includes taxes & fees
1 Mar - 2 Mar
Hanover Inn Dartmouth
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, (167 reviews)
"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 1,345 total
includes taxes & fees
2 Mar - 3 Mar
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Front of property

Castle Hill Resort And Spa

Castle Hill Resort And Spa
3.5 star property
Cavendish
9.0 out of 10, Wonderful, (108 reviews)
"Great place for a good price. "
United States
Matthew
The price is AED 821
AED 895 total
includes taxes & fees
23 Mar - 24 Mar
Castle Hill Resort And Spa
Smart TV, fireplace, books

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
9.8 out of 10, Exceptional, (104 reviews)
"Great Condo. We had plenty of space. Wendi was very responsive and even accommodated us checking in an hour early when we arrived in town. We would definitely come back. "
United States
Barbara M.
The price is AED 705
AED 1,308 total
includes taxes & fees
23 Mar - 24 Mar
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Property grounds

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, (28 reviews)
"Overall very clean and nice. Needs some updating like more spoons, only 2, bigger coffee cups. And a new coffee table that is very worn. "
United States
David A.
The price is AED 422
AED 1,159 total
includes taxes & fees
11 Mar - 12 Mar
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
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, (104 reviews)
"Had a wonderful stay. Clean,well kept and cozy."
United States
Edwin G.
The price is AED 951
AED 1,793 total
includes taxes & fees
23 Mar - 24 Mar
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Exterior

Two Double bed Hotel Room with outdoor heated pool 216

Two Double bed Hotel Room with outdoor heated pool 216
Killington
The price is AED 465
AED 684 total
includes taxes & fees
23 Mar - 24 Mar
Two Double bed Hotel Room with outdoor heated pool 216
Exterior

107 Deluxe Studio Queen, w/ Sleeper sofa w/ outdoor heated pool

107 Deluxe Studio Queen, w/ Sleeper sofa w/ outdoor heated pool
Killington
8.0 out of 10, Very Good, (7 reviews)
"Efficient and affordable option for a short stay."
United States
Marnie O.
The price is AED 465
AED 684 total
includes taxes & fees
29 Mar - 30 Mar
107 Deluxe Studio Queen, w/ Sleeper sofa w/ outdoor heated pool
Exterior

Deluxe One bedroom Queen Suite with outdoor heated pool 203

Deluxe One bedroom Queen Suite with outdoor heated pool 203
Killington
9.4 out of 10, Exceptional, (12 reviews)
"Convenient to Bear Lodge and town"
United States
Pamela T.
The price is AED 667
AED 958 total
includes taxes & fees
29 Mar - 30 Mar
Deluxe One bedroom Queen Suite with outdoor heated pool 203
Exterior

Cedarbrook Hotel Room 2 Doubles 119

Cedarbrook Hotel Room 2 Doubles 119
Killington
9.0 out of 10, Wonderful, (7 reviews)
"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 684 total
includes taxes & fees
29 Mar - 30 Mar
Cedarbrook Hotel Room 2 Doubles 119
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

Align Inn Vermont

Align Inn Vermont

10/10 Excellent
"As far as motels go, this was the best I ever stayed at! Our room was spotless, cleaning came in each day after 10 (which was fine because we were skiing). Free breakfast was good (the Jimmy Dean Breakfast Sandwiches were clutch) The staff was great, my kids loved the pool, and there was a delicious restaurant practically on site (The public house get the schnitzel you won't be disappointed) - A 7 min drive to Ski Quechee, 15 -20 min to NH- I can't say enough good things. "
Phil 3-night trip
Posted 2 days ago
Align Inn Vermont

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 22 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. Additionally, you'll find Okemo Mountain Resort in the area.
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.