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
Cottage in Gilboa
4.94 out of 5 average rating, 200 reviewsHome Alone Mountain Retreat
Nov 6 – 13
Cabin in Windham
4.88 out of 5 average rating, 110 reviewsThe Windham Cabin w/ Hot Tub
Aug 4 – 11
Condo in Hunter
4.98 out of 5 average rating, 535 reviewsHunter Mtn Liftside Ski In/Out, Slopeside!
Aug 6 – 13
Cabin in Chichester
4.99 out of 5 average rating, 514 reviewsGarden Cottage In The Catskills
Aug 21 – 28
Cottage in Roxbury
4.98 out of 5 average rating, 478 reviewsThe Little House
Apr 11 – 18
Home in Durham
4.96 out of 5 average rating, 101 reviewsWow! Panoramic Mountain View, Minutes to Windham!
Nov 7 – 14
Cabin in Maplecrest
4.94 out of 5 average rating, 163 reviewsFraxinus House - Ideal for Windham & Hunter
May 24 – 31
Condo in Windham
4.84 out of 5 average rating, 112 reviewsStudio 3 BEDS-SLEEP 4
Nov 12 – 19
Other great vacation rentals in Windham
Townhouse in Windham
4.92 out of 5 average rating, 38 reviewsSunny 3 BR Escape in Windham | The Mill House 2
Aug 22 – 29
Apartment in Windham
5.0 out of 5 average rating, 17 reviewsBlack Dome - a 2B, 2B Condo 5 min from Windham Mt.
May 24 – 31
Townhouse in Windham
5.0 out of 5 average rating, 57 reviewsCozy, peaceful-3Br (5 beds)2.5 Bath townhouse
Oct 29 – Nov 5
Guest suite in Windham
5.0 out of 5 average rating, 35 reviewsCozy 2 bedroom apartment with private entrance
Apr 17 – 24
Condo in Windham
4.97 out of 5 average rating, 58 reviewsBeautiful, modern, newly remodeled 1 bedroom condo
Oct 25 – Nov 1
Home in Hunter
5.0 out of 5 average rating, 57 reviewsModern House with Mountain View @Getawind
Oct 11 – 18
Home in Windham
5.0 out of 5 average rating, 33 reviewsNEW stylish Farm house on the golf course
Nov 16 – 23
Cabin in Gilboa
5.0 out of 5 average rating, 25 reviewsAuthentic Catskill Mtn. Cabin w/ Panoramic Views
Oct 5 – 12
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 townhouse rentals with a dedicated workspace in Windham?
Yes! Work meets play with ease at over 10 townhouse rentals in Windham featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in house rentals in Windham?
Experience the best of Windham with our house rentals, starting at about $140 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 condo rentals in Windham have wifi?
Absolutely! We offer over 20 condo rentals with wifi in Windham. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Windham have a bbq area?
Absolutely! We offer over 70 house 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 townhouse rentals in Windham?
Windham has more than 20 family-friendly townhouse 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 a bbq area, over 10 homes with self check-in, 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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