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 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Windham cottages

Property grounds

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.
$233 nightly
The price is $252
Oct 6 - Oct 7
Total with taxes and fees
Tiny House on Walnut Grove
Outdoor dining

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, (23 reviews)
"Great stay, lovely place, friendly host. Everything was perfect!"
United States
Taylor
$518 nightly
The price is $559
Sep 17 - Sep 18
Total with taxes and fees
Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants
Exterior

3. Romantic cottage with hot tub . Close to hiking and breweries . Pet friendly!

Romantic cottage with hot tub . Close to hiking and breweries . Pet friendly!
Phoenicia
9.8 out of 10, Exceptional, (33 reviews)
"Great place "
United States
Lisa R.
$173 nightly
The price is $194
Sep 17 - Sep 18
Total with taxes and fees
Romantic cottage with hot tub . Close to hiking and breweries . Pet friendly!
Terrace/patio

4. 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, (20 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.
$278 nightly
The price is $300
Sep 22 - Sep 23
Total with taxes and fees
Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
Property grounds

5. Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock
Woodstock
10.0 out of 10, Exceptional, (298 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.
$276 nightly
The price is $309
Sep 27 - Sep 28
Total with taxes and fees
Streamside Cottage Half Mile to Town of Woodstock
Exterior

6. Cozy 2-bedroom cottage in enchanting Catskill Mountains

Cozy 2-bedroom cottage in enchanting Catskill Mountains
Catskill
10.0 out of 10, Exceptional, (1 review)
"The property is great. Easy check-in and communication with host. Large property and comfortable beds."
United States
Robert G.
$468 nightly
The price is $506
Sep 17 - Sep 18
Total with taxes and fees
Cozy 2-bedroom cottage in enchanting Catskill Mountains
Exterior

7. 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.
$319 nightly
The price is $357
Sep 17 - Sep 18
Total with taxes and fees
Charming Cottage in the Heart of Catskill & Pet Friendly
Terrace/patio

8. Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
woodstock
8.8 out of 10, Excellent, (48 reviews)
"A gem just minutes from the heart of Woodstock!"
United States
Susannah H.
$278 nightly
The price is $311
Sep 21 - Sep 22
Total with taxes and fees
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
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

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

10/10 Excellent
"Everything was so smooth, from the detailed map and heads up of possible cell service interruptions, to the check in and check out process, housekeeping request, and the ease of communication via text. It was a perfect getaway, minimal interruptions, yet easy to reach with quick responses. Although I could tell there were other guests in cabins nearby because I would see parked cars, it was so quiet that I felt like I was truly there alone! They thought of everything as far as cookware, plates, cups for cold and hot drinks, and utensils. S’mores, snacks, water, coffee, tea, and use of firepit/firewood were all complimentary. There’s a fridge but no microwave which I was not expecting but useful to know. Bring seasoning if you plan to cook. Bring mosquito repellant. It was weird not having a sink in the bathroom but it wasn’t a big deal for me. Would definitely book again!"
crystal 2-night trip
Posted 5 hours ago
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Find out more about Windham

Windham Cottages information

Number of reviews
4,837
Accommodation
190 Cottages
Lowest Price
$109
Highest Price
$542

Frequently asked questions

How much do cottages in Windham cost?
Cottages in Windham range between $109 and $542 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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