Find Historic Hotels in Windham, VT

Start date: Check-in selected.
To Date
End date: Check-out

  • Upfront pricing

    Our total price for your stay includes taxes and fees

  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check availability on Windham Historic Hotels

Tonight
Dec 7 - Dec 8
Tomorrow
Dec 8 - Dec 9
Next weekend
Dec 12 - Dec 14
In two weeks
Dec 19 - Dec 21

Top Windham Historic Hotels

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
$327 nightly
The price is $366
Dec 15 - Dec 16
Total with taxes and fees
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Lobby lounge
Castle Hill Resort And Spa

Castle Hill Resort And Spa

3.5 star property
Cavendish
9.0 out of 10, Wonderful, (104)
"Convenient that there is a restaurant is in the Castle, we also loved the outdoor hot tub and pool. "
United States
Jeff
$251 nightly
The price is $274
Jan 6 - Jan 7, 2026
Total with taxes and fees
Castle Hill Resort And Spa
TV, books
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Walpole
10.0 out of 10, Exceptional, (8)
"Beautiful cozy cottage. Very clean. Wonderful host."
United States
Gloria A.
$227 nightly
The price is $246
Dec 8 - Dec 9
Total with taxes and fees
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
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.
$260 nightly
The price is $294
Dec 16 - Dec 17
Total with taxes and fees
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
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.
$251 nightly
The price is $271
Dec 8 - Dec 9
Total with taxes and fees
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Exterior detail
Entire Farmhouse with lots of open space 15 min north of Keene

Entire Farmhouse with lots of open space 15 min north of Keene

Walpole
10.0 out of 10, Exceptional, (38)
"Lovely place would definitely book again"
United States
Sean M.
$270 nightly
The price is $293
Dec 8 - Dec 9
Total with taxes and fees
Entire Farmhouse with lots of open space 15 min north of Keene
Property grounds
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.
$371 nightly
The price is $401
Dec 8 - Dec 9
Total with taxes and fees
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Interior
6 bed 7 Bath close to ski & shop w/ hot tub at Greybourne House in Manchester VT

6 bed 7 Bath close to ski & shop w/ hot tub at Greybourne House in Manchester VT

Manchester Center
10.0 out of 10, Exceptional, (51)
"This is our second time renting the Greybourne house. The house is just as amazing as we remembered it - spacious, clean, well stocked and located within a short drive to Stratton, Okemo or Killington. Allison is a great host - very responsive and helpful. We can't wait to return again next year."
United States
Masha S.
$1,718 nightly
The price is $1,941
Dec 15 - Dec 16
Total with taxes and fees
6 bed 7 Bath close to ski & shop w/ hot tub at Greybourne House in Manchester VT
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 Windham Hotel Reviews

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

10/10 Excellent
"Great place to stay while skiing at okemo"
Ken 1-night trip
Posted 1 day ago
Pointe at Castle Hill Resort

Frequently asked questions

What should a history buff expect from a stay in Windham?
The historical sites in Windham are likely at the top of your sightseeing list. And while you're here, why not also take some time enjoying all you'll find to see and do here?
How many historical hotels are there in Windham?
In Windham, there are 15 lodging options bookable on Expedia but not many designated as historic hotels.
What are the most important historical sites and other places to visit in Windham?
Notable places to visit in the surrounding area include Stratton Mountain Resort and Mount Snow. You'll also find Magic Mountain Ski Resort and Lowell Lake State Park in the area.
What is a historic hotel like in Windham?
By booking a historic hotel, guests can sleep in a place that has an officially recognized historic designation. A palace, castle, stately home or even a lodge, pub, or skyscraper can be considered a historic hotel provided that it's a place of special interest. Traditional architecture and period features are often found within the guestrooms or public spaces of such hotels in Windham, giving a real sense of character.
What is the difference between a historic hotel and a heritage hotel?
"Heritage hotel" is a term often used in Asia and Europe, wheareas the term "historic hotel" is more commonly used in the U.S. though overall the terms are quite similar. The physical building and architecture of historic hotels are generally the most important aspect. For a heritage hotel, mainly, it's cultural value as well as how it shaped the community.
Do historic hotels in Windham have modern facilities?
Hotels include modern conveniences and safety features you've come to expect, but every effort is made to preserve treasured traditions and historic facades. Private rooms with updated bathroom facilities, free WiFi, and the usual amenities found in any hotel will be available in a historic hotel. When you book a historic hotel in Windham, don't worry that you'll find a place that's uncomfortable or rundown.

Explore a world of travel with Expedia