Search Windham Cottage Accommodations

    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

In two weeks
5 Sept - 7 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov
In four months
12 Dec - 14 Dec

Featured Cottages in Windham

Our top choices for Windham cottages

Streamside Cottage Half Mile to Town of Woodstock
Property grounds

Streamside Cottage Half Mile to Town of Woodstock

10.0 out of 10, Exceptional, (249)
"A beautiful quiet setting! "
The price is AU$501
includes taxes & fees
4 Sept - 5 Sept
Streamside Cottage Half Mile to Town of Woodstock
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
Exterior

Junebug Cottage: peace, love and privacy a short walk to Woodstock village green

10.0 out of 10, Exceptional, (72)
"We were in Woodstock for a wedding. Junebug Cottage was perfect for our stay! "
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
Romantic cottage with hot tub . Close to hiking and breweries . Pet friendly!
Outdoor spa tub

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

9.8 out of 10, Exceptional, (20)
"Had a wonderful "
Romantic cottage with hot tub . Close to hiking and breweries . Pet friendly!
NEW! Herb Cottage: Historic Artist's Cottage, Wood Stove, Walk to Town!
TV, DVD player, books, video library

NEW! Herb Cottage: Historic Artist's Cottage, Wood Stove, Walk to Town!

9.8 out of 10, Exceptional, (135)
"We had a marvelous visit!"
NEW! Herb Cottage: Historic Artist's Cottage, Wood Stove, Walk to Town!
TOP RATED Romantic rustic luxury + flowing stream + walk to town = Brook Cottage
Exterior

TOP RATED Romantic rustic luxury + flowing stream + walk to town = Brook Cottage

10.0 out of 10, Exceptional, (166)
"The hosts had thought of everything to make our stay comfortable - lovely bright rooms, well stocked kitchen, plush linens and towels, within walking distance of all restaurants and shops and a beautiful stream and lawn outside! Excellent!"
TOP RATED Romantic rustic luxury + flowing stream + walk to town = Brook Cottage
Charming Cottage in Private Lake Community (Pet-Friendly!)
Fridge, microwave, oven, stovetop

Charming Cottage in Private Lake Community (Pet-Friendly!)

10.0 out of 10, Exceptional, (32)
"We enjoyed ourselves,relaxed,visited had a very enjoyable bisit"
Charming Cottage in Private Lake Community (Pet-Friendly!)
The Cabin at Chichester in the Catskills Mountains

The Cabin at Chichester in the Catskills Mountains

9.8 out of 10, Exceptional, (186)
"This is a great little cottage! It’s super clean and has everything you need and plenty of space inside and out. Host was terrific to deal with and made the process seamless and simple. Would definitely stay here again as a great place to stay while enjoying all the area has to offer!! "
The Cabin at Chichester in the Catskills Mountains
TOP-RATED! Pristine style+romantic luxury+firepit+walk to town=Brook Cottage Too
Exterior

TOP-RATED! Pristine style+romantic luxury+firepit+walk to town=Brook Cottage Too

10.0 out of 10, Exceptional, (119)
"The property was lovely, and the perfect location. Chelsea was great to work with!"
TOP-RATED! Pristine style+romantic luxury+firepit+walk to town=Brook Cottage Too
Rose Cottage
Outdoor dining

Rose Cottage

9.6 out of 10, Exceptional, (5)
"It's so peaceful there. It was lovely."
Rose Cottage
Private Home ~ All Yours ~ In town ~ fenced in yard ~ Hot Tub ~ Pets welcome!
Banquet hall

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."
Private Home ~ All Yours ~ In town ~ fenced in yard ~ Hot Tub ~ Pets welcome!
Catskills Home, 5 Mins to Windham Mtn Resort!
House (2 Bedrooms) | Front of property

Catskills Home, 5 Mins to Windham Mtn Resort!

3.0 star property
10.0 out of 10, Exceptional, (4)
"This place was awesome. Very clean, nicely appointed, very welcoming. Highly recommend and would definitely stay again. Only downside is that it is a second floor unit and the stairs are a little steep but still totally worth it "
Catskills Home, 5 Mins to Windham Mtn Resort!
4 Mi to Dtwn Catskill: Mtn-view Home
House (4 Bedrooms) | Interior

4 Mi to Dtwn Catskill: Mtn-view Home

3.0 star property
4 Mi to Dtwn Catskill: Mtn-view Home
Charming Cottage in the Heart of Catskill & Pet Friendly
Outdoor dining

Charming Cottage in the Heart of Catskill & Pet Friendly

10.0 out of 10, Exceptional, (14)
"Really enjoyed my stay! Very thoughtful host. "
Charming Cottage in the Heart of Catskill & Pet Friendly
Mountain Views & Brook Access: Home in Arkville!
House (3 Bedrooms) | Interior

Mountain Views & Brook Access: Home in Arkville!

3.0 star property
Mountain Views & Brook Access: Home in Arkville!
Experience Peace in this Beautiful country cottage nestled beneath the mountains
Property grounds

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 AU$493
includes taxes & fees
3 Sept - 4 Sept
Experience Peace in this Beautiful country cottage nestled beneath the mountains
Cabin 4 Mi to Belleayre Mountain: Ski, Hike & Fish
House (3 Bedrooms) | Interior

Cabin 4 Mi to Belleayre Mountain: Ski, Hike & Fish

3.0 star property
10.0 out of 10, Exceptional, (1)
"We had a great time during our stay. The house was nicely setup. We would go back again."
Cabin 4 Mi to Belleayre Mountain: Ski, Hike & Fish
Charming 2-bedroom cottage with WiFi and AC in fabulous Phoenicia
Outdoor spa tub

Charming 2-bedroom cottage with WiFi and AC in fabulous Phoenicia

10.0 out of 10, Exceptional, (4)
"Very kind and can tell they put a lot of effort in hosting"
Charming 2-bedroom cottage with WiFi and AC in fabulous Phoenicia
Cozy Catskills Cabin - 12 Mi to Windham Mountain!
House (2 Bedrooms) | Interior

Cozy Catskills Cabin - 12 Mi to Windham Mountain!

3.0 star property
10.0 out of 10, Exceptional, (1)
"It was great. Place was as advertised. Great place to stay, can't wait to book it again! Place was clean, easy to get in, has everything you would need for a long weekend getaway to the catskills."
Cozy Catskills Cabin - 12 Mi to Windham Mountain!
Modern Cottage with Private Pond, Spa and Views
Terrace/patio

Modern Cottage with Private Pond, Spa and Views

9.0 out of 10, Wonderful, (11)
"We arrived to a beautiful house overlooking vast forested mountains with a beautiful little pond with lots of froggy friends to watch. The hot tub was nice and we all got a good night sleep. Lots of good hikes around and lots of little towns to visit and pop into for a book or coffee. Great stay!"
Modern Cottage with Private Pond, Spa and Views
Catskills Mtn Retreat w/ Panoramic View & Fire Pit
House (3 Bedrooms) | Interior

Catskills Mtn Retreat w/ Panoramic View & Fire Pit

3.0 star property
Catskills Mtn Retreat w/ Panoramic View & Fire Pit
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

Hotel Vienna

Hotel Vienna

10/10 Excellent
"Beautiful property. Lovely room with a very comfortable bed. Extremely helpful desk staff—I would like to extend my thanks especially to her. "
Laura 1-night trip
Posted 2 days ago
Hotel Vienna

Frequently asked questions

What is there to do in Windham near my cottage?
Once you've unpacked your things and settled in, venture out and discover the fantastic things Windham has on offer. Hunter Mountain is a great attraction to add to your must-do list.