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

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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
$165 nightly
The price is $182
Oct 12 - Oct 13
Total with taxes and fees
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
$303 nightly
The price is $339
Oct 22 - Oct 23
Total with taxes and fees
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.
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Top Windham Hotel Reviews

SunView Motel

SunView Motel

10/10 Excellent
"We were happy with our stay. The room was clean, parking was easy, and the staff were friendly."
Bryan 1-night trip
Posted 6 hours ago
SunView Motel

Find out more about Windham

Windham Guest Houses information

Number of reviews
141
Accommodation
8 Guest Houses
Lowest Price
$182
Highest Price
$339

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 $182 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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