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Check prices for these dates

In two weeks
Jun 5 - Jun 7
In two months
Jul 17 - Jul 19
In three months
Aug 14 - Aug 16
In four months
Sep 11 - Sep 13

Our top choices for Windham cottages

Property grounds

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.
$260 nightly
The price is $280
May 25 - May 26
Total with taxes and fees
Tiny House on Walnut Grove
Exterior

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

Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
Catskill
9.6 out of 10, Exceptional, (15 reviews)
"Host was super welcoming - the pace was gorgeous and had everything we could possibly need! Fabulous stay overall"
United States
Athena P.
$287 nightly
The price is $310
Jun 2 - Jun 3
Total with taxes and fees
Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
Exterior

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, (24 reviews)
"Clean and cozy with great amenities! Would come back!"
United States
Kristen B.
$315 nightly
The price is $353
May 25 - May 26
Total with taxes and fees
Charming Cottage in the Heart of Catskill & Pet Friendly
Outdoor dining

Modern Cottage 2 (The Lorca, Catskills) - 10 min to Belleayre, 25 min to Windham

Modern Cottage 2 (The Lorca, Catskills) - 10 min to Belleayre, 25 min to Windham
Shandaken
10.0 out of 10, Exceptional, (1 review)
"10/10 experience. beautiful cabin, super cozy"
United States
Hunter W.
$204 nightly
The price is $228
Jun 3 - Jun 4
Total with taxes and fees
Modern Cottage 2 (The Lorca, Catskills) - 10 min to Belleayre, 25 min to Windham
Terrace/patio

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
woodstock
9.0 out of 10, Wonderful, (47 reviews)
"A gem just minutes from the heart of Woodstock!"
United States
Susannah H.
$277 nightly
The price is $310
May 31 - Jun 1
Total with taxes and fees
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Outdoor dining

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, (22 reviews)
"Great stay, lovely place, friendly host. Everything was perfect!"
United States
Taylor
$517 nightly
The price is $558
May 25 - May 26
Total with taxes and fees
Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants
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
"The hotel is centrally located. A lot of shops, bars and restaurants are within walking distance. Overall, I loved it and highly recommend it. Staff and coffee service in the morning was great. Lit tile issue with room key was taken care of immediately and I was given an upgrade without requesting it."
Rafael 2-night trip
Posted 7 hours ago
Woodstock Way Hotel

Find out more about Windham

Windham Cottages information

Number of reviews
87
Accommodation
181 Cottages
Lowest Price
$228
Highest Price
$558

Frequently asked questions

How much do cottages in Windham cost?
Cottages in Windham range between $228 and $558 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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