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 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10

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, (298 reviews)
"It's a nice spot to stay while in this area."
United States
Gustavo
$144 nightly
The price is $158
Dec 15 - Dec 16
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, (148 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
$351 nightly
The price is $394
Dec 14 - Dec 15
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

Emerson Resort & Spa

Emerson Resort & Spa

8/10 Good
"I loved my stay. The room was beautiful and clean. The tub was exceptional especially after the hiking. I would definitely come back. Please make sure I have put the highest rating. My screen is making the text too large. I was only able to get to GOOD. If there is a higher rating please change it to exceptional, etc ."
Mary Rose 1-night trip
Posted 22 hours ago
Emerson Resort & Spa

Find out more about Windham

Windham Guest Houses information

Number of reviews
446
Accommodation
9 Guest Houses
Lowest Price
$158
Highest Price
$394

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 $158 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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