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

Check prices for these dates

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3

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, (297 reviews)
"I had a wonderful stay at Shadowcrest! The aesthetic was incredibly nice and cozy, making it the perfect place to relax. The host was also super kind and helpful throughout my visit. I highly recommend staying here!"
United States
Andres
$142 nightly
The price is $156
Dec 9 - Dec 10
Total with taxes and fees
Shadowcrest
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 Windham Hotel Reviews

Kaatskill Mountain Club & Condos by Vail Resorts

Kaatskill Mountain Club & Condos by Vail Resorts

10/10 Excellent
"We had a wonderful weekend! Clean, spacious and very well kept! Updated televisions, full kitchen and everything you need! Would absolutely stay again!"
Michelle 1-night trip
Posted less than an hour ago
Kaatskill Mountain Club & Condos by Vail Resorts

Find out more about Windham

Windham Guest Houses information

Number of reviews
Accommodation
9 Guest Houses
Lowest Price
$156
Highest Price
$156

Frequently asked questions

What is the nightly rate for a guest house in Windham?
Rates for Windham guest houses vary, but travelers can find great-value prices from $156 with Expedia. A range of factors can affect nightly rates, such as the location, the breakfast offering, and the range of amenities. Travelers looking for a good deal should consider looking for a midweek stay, as weekend rates at Windham guest houses tend to be higher. Remember to also use our filters to sort prices from low to high.
Are there any family-friendly guest houses in Windham?
Beds on Clouds is a delightful choice for families visiting Windham, NY. This charming guest house has a friendly setting where you can truly unwind after a day filled with adventure. Families will appreciate the daily housekeeping, ensuring your space remains tidy and comfortable throughout your stay.
What's the difference between a Windham guest house and a B&B?
A guest house in Windham is typically a larger establishment with more rooms, offering a more hotel-like experience, and may provide additional amenities including luxury bedding. In contrast, a B&B is usually a smaller property that focuses primarily on providing a room and breakfast. A B&B is often more personal, and breakfast is typically included as part of the stay, but other services might be more limited compared to a guest house.

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