Search Guest Houses in Windham

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Dec 19 - Dec 21
In two weeks
Dec 26 - Dec 28
In one month
Jan 9 - Jan 11
In two months
Feb 6 - Feb 8

Our top choices for Windham guest houses

Porch
Beds on Clouds

Beds on Clouds

Beds on Clouds
3.0 star property
Windham
7.4 out of 10, Good, (68)
"Great spot for a weekend getaway"
United States
Bertrand
$189 nightly
The price is $204
Dec 15 - Dec 16
Total with taxes and fees
Beds on Clouds
Front of property
Shadowcrest

Shadowcrest

Shadowcrest
3.5 star property
Fleischmanns
9.8 out of 10, Exceptional, (264)
"Shadowcrest is a gem and instantly felt like a home away from home. The bed was incredibly comfortable, the shower was amazing, and Brendan is extremely charming, informative and hospitable. Will absolutely be staying again and again!"
United States
Robert
$145 nightly
The price is $160
Dec 16 - Dec 17
Total with taxes and fees
Shadowcrest
Outdoor spa tub
The Herwood Inn

The Herwood Inn

The Herwood Inn
4.5 star property
Woodstock
9.6 out of 10, Exceptional, (90)
"Just lovely all around! I loved the attention to detail inside and on the grounds."
United States
karen
$172 nightly
The price is $193
Dec 15 - Dec 16
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

Hotel Vienna

Hotel Vienna

10/10 Excellent
"Love this place when its available. Low key, clean and conveniently near BOTH Hunter and Windham ski areas!"
Bruce 1-night trip
Posted 2 days ago
Hotel Vienna

Find out more about Windham

Windham Guest Houses information

Number of reviews
421
Accommodation
9 Guest Houses
Lowest Price
$160
Highest Price
$204

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 $160 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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