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

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Windham cottages

A snow-covered ground with footprints leading to a house with a solar panel roof.

1. Tiny House on Walnut Grove

Tiny House on Walnut Grove
Ashland
4.0 out of 10, (2 reviews)
"Many problems with this listing, first the fire alarm was low on battery, I had to physically climb to reach the smoke detector to detach and remove the battery, a sharp beeping noise went off every 90 seconds and we wouldn’t have been able to sleep without stopping it. There were no spare batteries to change. There were spiders everywhere. My friend used the shower and saw 11 of them moving around the ceiling. They were in the main bed and on the counter and sink as well. The tenant was nice...
United States
Trevor C.
$398 nightly
The price is $429
Oct 3 - Oct 4
Total with taxes and fees
Tiny House on Walnut Grove
A wooden deck with a white railing, surrounded by lush green trees.

2. Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants

Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants
Maplecrest
10.0 out of 10, Exceptional, (24 reviews)
"Great stay, lovely place, friendly host. Everything was perfect!"
United States
Taylor
$518 nightly
The price is $559
Oct 4 - Oct 5
Total with taxes and fees
Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants
A covered porch with a wooden bench, a wicker chair, and a sofa with cushions.

3. Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill

Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
Catskill
9.8 out of 10, Exceptional, (21 reviews)
"The property was just as described, very private and cozy. We enjoyed the large balcony as well as the yard. There were also several nice hiking trails close by. Overall we were very happy with our stay."
United States
Ryan P.
$280 nightly
The price is $302
Oct 5 - Oct 6
Total with taxes and fees
Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
A single-story house with a dark exterior, a chimney, and a small window.

4. Cozy 2-bedroom cottage in enchanting Catskill Mountains

Cozy 2-bedroom cottage in enchanting Catskill Mountains
Catskill
10.0 out of 10, Exceptional, (2 reviews)
"The property is great. Easy check-in and communication with host. Large property and comfortable beds."
United States
Robert G.
$471 nightly
The price is $509
Oct 3 - Oct 4
Total with taxes and fees
Cozy 2-bedroom cottage in enchanting Catskill Mountains
A wooden cabin surrounded by lush greenery and trees.

5. Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock
Woodstock
10.0 out of 10, Exceptional, (301 reviews)
"It was the perfect place for a weekend away from home! The location was only a few minutes from town and was the perfect size for a couple. Would definitely reccomend!"
United States
Kristen S.
$313 nightly
The price is $351
Oct 20 - Oct 21
Total with taxes and fees
Streamside Cottage Half Mile to Town of Woodstock
A single-story house with a black front door, two windows on either side, and two black trash bins in front.

6. Charming Cottage in the Heart of Catskill & Pet Friendly

Charming Cottage in the Heart of Catskill & Pet Friendly
Catskill
10.0 out of 10, Exceptional, (26 reviews)
"Everything was great! The house is in a great location and is very clean, modern and cozy. I would highly recommend staying here! "
United States
Dave P.
$318 nightly
The price is $356
Oct 6 - Oct 7
Total with taxes and fees
Charming Cottage in the Heart of Catskill & Pet Friendly
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

Woodstock Way Hotel

Woodstock Way Hotel

10/10 Excellent
"We really enjoyed our stay at the Woodstock Way. We had a beautiful view of the waterfall and stream and enjoyed the balcony. The bubbling water and surrounding woods made it feel like a retreat, but we were a short walk away from cute and quirky places to grab breakfast or lunch and shop. It was a very unique experience and my only regret was that I didn't book an additional day (or two),"
Dona 2-night trip
Posted 15 hours ago
Woodstock Way Hotel

Find out more about Windham

Windham Cottages information

Number of reviews
350
Accommodation
190 Cottages
Lowest Price
$302
Highest Price
$559

Frequently asked questions

How much do cottages in Windham cost?
Cottages in Windham range between $302 and $559 per night. These stays offer a chance to touch base with nature — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why book your cottage in Windham with Expedia?
Expedia has some wonderful cottages in Windham, so get set for a memorable stay on nature's doorstep. If you have a budget, select how much you want to spend and the preferred star rating of your property. Or, try out our filters to search for cottages with a pool or a hot tub. We'll help you find the right place whatever your style of travel or plans.
How can I find cheap cottages in Windham?
With Expedia's convenient filter tool, sourcing cheap cottages in Windham is a snap. To discover stays that are friendly on the wallet, tailor your search results by budget, star rating and amenities.
What is there to do in Windham near my cottage?
If you're eager to fill up your itinerary in Windham, be sure to visit Windham Mountain Resort. It's popular among travelers and locals alike.

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