Search Cottages in Windham

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Cottages in Windham and around

Tiny House on Walnut Grove
Property grounds

Tiny House on Walnut Grove

2.0 star property
4.0 out of 10, (1)
The price is €247
includes taxes & fees
14 Sept - 15 Sept
Tiny House on Walnut Grove
Country Cottage with beautiful views and easy access to Catskills activities.
Exterior

Country Cottage with beautiful views and easy access to Catskills activities.

10.0 out of 10, Exceptional, (10)
"Great spot!"
The price is €156
includes taxes & fees
18 Aug - 19 Aug
Country Cottage with beautiful views and easy access to Catskills activities.
Experience Peace in this Beautiful country cottage nestled beneath the mountains
Exterior

Experience Peace in this Beautiful country cottage nestled beneath the mountains

10.0 out of 10, Exceptional, (6)
"Nice house, well stocked and nice outdoor area/deck."
The price is €286
includes taxes & fees
2 Sept - 3 Sept
Experience Peace in this Beautiful country cottage nestled beneath the mountains
Streamside Cottage Half Mile to Town of Woodstock
Exterior

Streamside Cottage Half Mile to Town of Woodstock

10.0 out of 10, Exceptional, (248)
"A beautiful quiet setting! "
The price is €297
includes taxes & fees
2 Sept - 3 Sept
Streamside Cottage Half Mile to Town of Woodstock
The Lily Pad - Hunter, NY
Exterior

The Lily Pad - Hunter, NY

The Lily Pad - Hunter, NY
Modern Cottage 2 (The Lorca, Catskills) - 10 min to Belleayre, 25 min to Windham
Exterior

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
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Terrace/patio

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

9.0 out of 10, Wonderful, (42)
"This is a great place to stay. Really loved the fire pit by the creek for evening cocktails and conversation."
The price is €262
includes taxes & fees
14 Sept - 15 Sept
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants
Outdoor dining

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

10.0 out of 10, Exceptional, (20)
"We had a wonderful stay at the cottage. Place was perfect and met all our needs. The cottage was lovely and cozy, truly home away from home. The host, Agnes, was kind and very helpful. Will definitely be back."
The price is €482
includes taxes & fees
15 Sept - 16 Sept
Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants
Private Home ~ All Yours ~ In town ~ fenced in yard ~ Hot Tub ~ Pets welcome!
Exterior

Private Home ~ All Yours ~ In town ~ fenced in yard ~ Hot Tub ~ Pets welcome!

9.8 out of 10, Exceptional, (116)
"The location was exceptional, close to restaurants and shops, quiet neighborhood, comfortable bed and the house was well stocked with everything you’d need."
The price is €637
includes taxes & fees
23 Aug - 24 Aug
Private Home ~ All Yours ~ In town ~ fenced in yard ~ Hot Tub ~ Pets welcome!
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windham Hotel Reviews

Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark

10/10 Excellent
"Great location. Beautiful resort. Great and helpful staff"
Shirley 2-night trip
Posted 2 days ago
Hunter Lodge, a Bluebird by Lark

Frequently asked questions

How much do cottages in Windham cost?
Cottages in Windham range between €262 and €637 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.