Find Historic Hotels in Windsor, VT

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Windsor Historic Hotels

Tonight
26 Mar - 27 Mar
Tomorrow
27 Mar - 28 Mar
This weekend
27 Mar - 29 Mar
Next weekend
3 Apr - 5 Apr

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, (928 reviews)
"Perfect stay: best service, location, and ambiance!"
United States
Elena
The price is AED 834
AED 905 total
includes taxes & fees
5 Apr - 6 Apr
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, (168 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 1,308 total
includes taxes & fees
30 Mar - 31 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, (113 reviews)
"nice place"
United States
armin
The price is AED 601
AED 655 total
includes taxes & fees
1 Apr - 2 Apr
Castle Hill Resort And Spa
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, (108 reviews)
"We enjoyed our stay, the house was lovely and close to everything in Ludlow and Okemo."
United States
Hannah M.
The price is AED 853
AED 1,694 total
includes taxes & fees
30 Mar - 31 Mar
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
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 518
AED 1,075 total
includes taxes & fees
20 Apr - 21 Apr
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, (30 reviews)
"Great property, clean and close to the slope"
United States
tiliger01
The price is AED 206
AED 854 total
includes taxes & fees
8 Apr - 9 Apr
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
TV

Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck

Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck
Plymouth
9.8 out of 10, Exceptional, (24 reviews)
"The Nest at Hawk Ledges was a perfect summer getaway. The home provides comfort in a tranquil setting while being close enough to many summer adventures. We enjoyed relaxing in the bright, open home after taking many day trips to explore the area. What a gem!"
United States
Ben N.
The price is AED 716
AED 2,612 total
includes taxes & fees
16 Apr - 17 Apr
Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck
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
6 Apr - 7 Apr
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 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
29 Mar - 30 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.
View all properties

Top Windsor Hotel Reviews

Best Western West Lebanon-Hanover Hotel

Best Western West Lebanon-Hanover Hotel

4/10 Poor
"I’ve stayed in budget hotels before, but this was on another level entirely. The room clearly hadn’t been properly cleaned in a long time. The floor was full of crumbs, and there was literally a pile of Cheerios sitting under the door to the connecting room. That alone should have been a red flag. It didn’t get better from there. The shower mat looked like something had chewed a hole straight through it. honestly, it looked like a mouse had been at it. Not exactly what you want to see in a place you’re supposed to relax. The sheets were just as bad; old, rough, and so worn they felt like you were sleeping on sandpaper. To top it all off, I got an automated text at 6:01 a.m. asking how my stay was. Who sends that kind of message that early? If anything, it just highlighted how out of touch the place is with basic guest experience. The only positive is the location—it’s convenient. But that’s not nearly enough to make up for everything else. I wouldn’t stay here again under any circumstances. "
Elicia 1-night trip
Posted 8 hours ago
Best Western West Lebanon-Hanover Hotel

Explore a world of travel with Expedia

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.