Find Historic Hotels in Windsor, VT

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Check availability on Windsor Historic Hotels

Tonight
5 Mar - 6 Mar
Tomorrow
6 Mar - 7 Mar
This weekend
6 Mar - 8 Mar
Next weekend
13 Mar - 15 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, (920 reviews)
"Friendly. Clean, good location"
United States
Deborah
The price is AED 834
AED 905 total
includes taxes & fees
8 Mar - 9 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
9 Mar - 10 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 830
AED 905 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, (106 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 702
AED 1,287 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 404
AED 1,132 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, (107 reviews)
"Had a wonderful stay. Clean,well kept and cozy."
United States
Edwin G.
The price is AED 929
AED 1,764 total
includes taxes & fees
25 Mar - 26 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

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 reviews)
"It was fine for our 1 night stay in the area. When I booked I did not realize that this is a motel."
United States
Laura D.
The price is AED 465
AED 684 total
includes taxes & fees
31 Mar - 1 Apr
Queen Studio on the 2nd floor with outdoor heated pool 207
Exterior

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
8.8 out of 10, Excellent, (14 reviews)
"My fiancé and I needed a quiet fall retreat and this was the perfect place! Situated right in Killington we were super close to restaurants and secluded enough that it felt like our own little fall hideaway. The property was clean and the room was phenomenal for the price with a full kitchen and living area. There is even a heated pool that was so lovely to relax in after our packed day of activities. It was a short drive to Woodstock and the leaves were just hitting peak season during our stay....
United States
Catherine T.
The price is AED 667
AED 958 total
includes taxes & fees
23 Mar - 24 Mar
Deluxe One bedroom Queen Suite on the 2nd floor with outdoor heated pool 209
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

On The River Inn

On The River Inn

10/10 Excellent
"The breakfast and staff were AMAZING! Freshly made scrambled eggs, bacon, sausage patties, french toast, waffles, Cabot yogurt with all the fixings, dry cereal, hot oatmeal, breads, muffins, danish, etc. Everything was delicious and well presented as well! Forgot to mention freshly gound coffee! YUM! KUDOS!"
Elizabeth 2-night trip
Posted 1 hour ago
On The River Inn

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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 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. 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.