Windham vacation rentals
Book unique vacation rentals, houses, and more on Airbnb
Top-rated vacation rentals in Windham
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Windham vacation rentals
Stay near Windham's top sights
Other great vacation rentals in Windham
Guest suite in Windham
4.93 out of 5 average rating, 111 reviewsCozy Cabin Condo by the Mountain, 5mins to skiing!
Home in Catskill
4.99 out of 5 average rating, 136 reviewsAthens, NY House - 1 Bedroom "Want to Get Away"?
Home in Prattsville
4.91 out of 5 average rating, 273 reviewsYanity House
Cabin in Kingston
4.99 out of 5 average rating, 336 reviewsCome Stay in "The Shoe"
Cottage in Roxbury
4.98 out of 5 average rating, 483 reviewsThe Little House
Tiny home in Lexington
4.95 out of 5 average rating, 304 reviewsDiamond Notch - Mini A-frame, Spectacular Views
Cottage in Kinderhook
4.98 out of 5 average rating, 177 reviewsThe Cottage on Sylvester Street
Cabin in Jefferson
5.0 out of 5 average rating, 436 reviews"Far from the Madding Crowd" Cozy Cabin Retreat
Other great vacation rentals in Windham
Cabin in West Kill
4.97 out of 5 average rating, 175 reviewsWest Kill Cabin
Home in Cornwallville
4.98 out of 5 average rating, 102 reviewsPrivate Waterfall Retreat on 10 acres
Cabin in Catskill
4.95 out of 5 average rating, 152 reviewsRestorative Escape in the Woods with Sauna
Cabin in Boiceville
5.0 out of 5 average rating, 128 reviewsCome enjoy our wee cabin!
Bungalow in Cairo
4.99 out of 5 average rating, 314 reviewsSwim just feet from your door, 20 min to Hudson
Home in Durham
4.95 out of 5 average rating, 20 reviewsCharming retreat near Windham NY
Guesthouse in Windham
4.99 out of 5 average rating, 96 reviewsAlpine Chalet on Spectacular Property
Cabin in Gilboa
5.0 out of 5 average rating, 32 reviewsAuthentic Catskill Mtn. Cabin w/ Panoramic Views
Quick stats about vacation rentals in Windham
Total rentals
160 properties
Rentals with a pool
20 properties have a pool
Pet-friendly rentals
50 properties allow pets
Family-friendly rentals
150 properties are a good fit for families
Total number of reviews
5.6K reviews
Nightly prices starting at
$70 before taxes and fees
Frequently Asked Questions
Are there condo rentals with a dedicated workspace in Windham?
Yes! Work meets play with ease at over 10 condo rentals in Windham featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in apartment rentals in Windham?
Experience the best of Windham with our apartment rentals, starting at about $90 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Windham have self check-in?
Absolutely! We offer over 50 house rentals with self check-in in Windham. Enjoy a tailored experience with all the comforts you desire.
Do townhouse rentals in Windham have wifi?
Absolutely! We offer over 20 townhouse rentals with wifi in Windham. Enjoy a tailored experience with all the comforts you desire.
Do cabin rentals in Windham have a bbq area?
Absolutely! We offer over 10 cabin rentals with a bbq area in Windham. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Windham have a gym?
Absolutely! We offer over 10 house rentals with a gym in Windham. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly house rentals in Windham?
Four-legged friends are welcome in Windham. Choose from more than 20 house rentals for guests traveling with pets.
Are there family-friendly house rentals in Windham?
Windham has more than 70 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for Cabin Rentals in Windham?
Enhance your stay in our Cabin Rentals with the most popular amenities: over 10 homes with self check-in, over 10 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there Windham vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 20 vacation homes with pools in Windham, available on Airbnb. Make a splash and soak up the sun in style!
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