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
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

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.
$384 nightly
The price is $414
Nov 16 - Nov 17
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, (25 reviews)
"Great stay, lovely place, friendly host. Everything was perfect!"
United States
Taylor
$499 nightly
The price is $539
Nov 15 - Nov 16
Total with taxes and fees
Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants
A wooden deck with a table and chairs, overlooking a snowy landscape with bare trees.

3. 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, (2 reviews)
"It was a charming and cozy cabin nested in the woods. Perfect size for two people."
United States
afsoon p.
$165 nightly
The price is $184
Nov 30 - Dec 1
Total with taxes and fees
Modern Cottage 2 (The Lorca, Catskills) - 10 min to Belleayre, 25 min to Windham
A wooden deck with a railing, leading to a covered area with a view of a road and greenery.

4. Game Room & Fire Pit! Creekside Catskills Retreat

Game Room & Fire Pit! Creekside Catskills Retreat
3.0 star property
Tannersville
$603 nightly
The price is $651
Nov 15 - Nov 16
Total with taxes and fees
Game Room & Fire Pit! Creekside Catskills Retreat
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, (309 reviews)
"perfect for a quiet getaway for 2."
United States
Anonymous traveler
$268 nightly
The price is $300
Nov 15 - Nov 16
Total with taxes and fees
Streamside Cottage Half Mile to Town of Woodstock
A covered porch with a wooden bench, a wicker chair, and a sofa with cushions.

6. 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)
"Artsy, comfortable and cozy cottage in a country setting. Love the deck for grilling! This was our second time here and we hope to be back again!"
United States
Laura G.
$284 nightly
The price is $307
Nov 16 - Nov 17
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.

7. 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.
$451 nightly
The price is $487
Nov 16 - Nov 17
Total with taxes and fees
Cozy 2-bedroom cottage in enchanting Catskill Mountains
A single-story house with a black front door, two windows on either side, and two black trash bins in front.

8. 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, (31 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.
$315 nightly
The price is $353
Nov 15 - Nov 16
Total with taxes and fees
Charming Cottage in the Heart of Catskill & Pet Friendly
A covered outdoor area with wooden benches and a view of a green landscape.

9. Mtn-view Luxe Catskills Retreat for Groups

Mtn-view Luxe Catskills Retreat for Groups
3.0 star property
Hobart
$642 nightly
The price is $706
Nov 15 - Nov 16
Total with taxes and fees
Mtn-view Luxe Catskills Retreat for Groups
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 21 hours ago
Emerson Resort & Spa

Find out more about Windham

Windham Cottages information

Number of reviews
52
Accommodation
186 Cottages
Lowest Price
$184
Highest Price
$706

Frequently asked questions

How much do cottages in Windham cost?
Cottages in Windham range between $184 and $706 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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