A winding road through a forest with autumn foliage, a rocky cliff on the right, and a mountain in the background.

Search Guest Houses in Windham from CA $207

  • 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 prices for these dates

Next weekend
Oct 16 - Oct 18
In two weeks
Oct 23 - Oct 25
In one month
Nov 6 - Nov 8
In two months
Dec 4 - Dec 6

Our top choices for Windham guest houses

A large, white, two-story house with a turret and a wrap-around porch, surrounded by lush greenery.

1. Shadowcrest

Shadowcrest
3.5 star property
Fleischmanns
9.8 out of 10, Exceptional, (291 reviews)
"The house is beautiful and our room lovely . Will stay again"
Canada
David
The price is CA $188
CA $207 total
includes taxes & fees
Oct 12 - Oct 13
Shadowcrest
A modern house with a wooden deck, a fire pit, and a covered outdoor seating area.

2. The Herwood Inn

The Herwood Inn
4.0 star property
Woodstock
9.6 out of 10, Exceptional, (141 reviews)
"Wonderful experience! The room was beautiful and equipped with everything you could think of. We had such a lovely,relaxing stay."
United States
Diana
The price is CA $417
CA $467 total
includes taxes & fees
Oct 22 - Oct 23
The Herwood Inn
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windham Hotel Reviews

AutoCamp Catskills

AutoCamp Catskills

8/10 Good
"Our stay was great , we really enjoyed the clubhouse the boardgames, a small hike on the property and the airstream was nicely equipped with outside grill, smart tv, and very nice outdoor space. Cleaning wise it was okay, we found hair in the shower drain, futon cover felt unwashed and I wish they had coffee in the clubhouse throughout the day. Would definitely recommend it!"
Mehwish 2-night trip
Posted 4 hours ago
AutoCamp Catskills

Find out more about Windham

Windham Guest Houses information

Number of reviews
141
Accommodation
8 Guest Houses
Lowest Price
CA $207
Highest Price
CA $467

Explore a world of travel with Expedia