House vacation rentals in Windham
Find and book unique houses on Airbnb
Top-rated house rentals in Windham
Guests agree: these houses 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 house rentals
House rentals with a pool
Home in Woodstock
4.98 out of 5 average rating, 100 reviewsWoodstock Historic Artist Estate- The Museum House
Jan. 15 – 22
Home in Prattsville
4.91 out of 5 average rating, 125 reviewsLuxury Retreat in Lexington
Dec. 29 – Jan. 5
Home in Ghent
4.87 out of 5 average rating, 270 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
Nov. 15 – 22
Home in Kerhonkson
4.94 out of 5 average rating, 325 reviewsCountry House: Rustic Charm With Modern Feel
May 14 – 21
Home in Woodstock
4.91 out of 5 average rating, 210 reviewsJapanese Teahouse & Onsen, outside shower, tennis
Nov. 9 – 16
Home in Saugerties
4.96 out of 5 average rating, 150 reviewsLux 1800's renovated farmhouse w/hot tub+pool
Oct. 16 – 23
Home in Saugerties
5.0 out of 5 average rating, 132 reviewsUpstate Modern Scandinavian Barn in the Catskills
Oct. 31 – Nov. 7
Home in Hunter
4.92 out of 5 average rating, 158 reviewsCharming cabin with Hunter Mountain views
Jun. 20 – 27
Weekly house rentals
Home in Lanesville
4.92 out of 5 average rating, 210 reviewsRoseland, Streamside 1865 house. 7 min to slopes
Nov. 14 – 21
Home in Jewett
4.79 out of 5 average rating, 102 reviewsTwin Cabin I- Hot Tub & Fireplace Hiking Retreat
May 16 – 23
Home in Jewett
4.96 out of 5 average rating, 156 reviewsLast minute deal! BBQ hut, She shed, Pizza oven
Sep. 13 – 20
Home in Jewett
4.81 out of 5 average rating, 114 reviewsCozy Cabin Retreat with Hot Tub & Fire Pit
Jul. 15 – 22
Home in Catskill
4.96 out of 5 average rating, 135 reviewsHEAVEN ON EARTH - Hudson Riverfront Home
Dec. 27 – Jan. 3
Home in Windham
4.87 out of 5 average rating, 127 reviewsLive the Slow Life at an All-Season Mountain Escape
Nov. 14 – 21
Home in Roxbury
5.0 out of 5 average rating, 125 reviewsPrivate 3BR escape w/ sweeping Mt Views & Firepit!
Apr. 8 – 15
Home in Durham
4.95 out of 5 average rating, 20 reviewsCharming retreat near Windham NY
Sep. 13 – 20
Private house rentals
Home in Gilboa
4.85 out of 5 average rating, 40 reviewsGreat for hunters-skiers-hikers close to Windham
May 5 – 12
Home in Windham
5.0 out of 5 average rating, 33 reviewsNEW stylish Farm house on the golf course
Aug. 23 – 30
Home in Windham
4.91 out of 5 average rating, 58 reviewsModern Ski House Minutes From The Slopes
Oct. 29 – Nov. 5
Home in Windham
4.96 out of 5 average rating, 52 reviewsBluebird Cabin: Modern Home With Ski Windham View
Nov. 16 – 23
Home in Cornwallville
4.98 out of 5 average rating, 98 reviewsPrivate Waterfall Retreat on 10 acres
Nov. 24 – Dec. 1
Home in Windham
4.94 out of 5 average rating, 31 reviewsFunky round home with views of Windham mountain!
Mar. 7 – 14
Home in Windham
5.0 out of 5 average rating, 10 reviewsModern Windham Swiss Chalet
Sep. 21 – 28
Home in Windham
4.95 out of 5 average rating, 40 reviewsPrivate 5 acre Windham Mountain Ski Retreat
Oct. 21 – 28
Quick stats about house rentals in Windham
Total rentals
70 properties
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
70 properties are a good fit for families
Total number of reviews
2.2K reviews
Nightly prices starting at
$191 CAD before taxes and fees
Destinations to explore
- New City Vacation rentals
- New Haven Vacation rentals
- Lake George Vacation rentals
- Mount Pocono Vacation rentals
- Washington Vacation rentals
- Philadelphia Vacation rentals
- Jersey City Vacation rentals
- New York Vacation rentals
- Mississauga Vacation rentals
- The Hamptons Vacation rentals
- Boston Vacation rentals
- Montreal Vacation rentals
- Earth house rentals United States
- Lighthouse rentals United States
- Guesthouse rentals United States
- Townhouse rentals United States
- House rentals United States
- House rentals New York
- Treehouse rentals New York
- Townhouse rentals New York
- Tiny house rentals New York
- Guesthouse rentals New York
- House rentals New York
- Treehouse rentals New York
- Townhouse rentals New York
- Tiny house rentals New York
- Guesthouse rentals New York
- Townhouse rentals Connecticut
- Lake house rentals Connecticut
- Tiny house rentals Connecticut
- Beach house rentals Connecticut
- Guesthouse rentals Connecticut
- House rentals Connecticut
- Fitness-friendly rentals Windham
- Condo rentals Windham
- Monthly Rentals Windham
- Rentals with outdoor seating Windham
- Rentals with pools Windham
- Kid-friendly rentals Windham
- Townhouse rentals Windham
- Ski-in/ski-out rentals Windham
- Family-friendly rentals Windham
- Chalet rentals Windham
- Pet-friendly rentals Windham
- Rentals with a patio Windham
- Rentals with a washer and dryer Windham
- Rentals with a firepit Windham
- Rentals with a hot tub Windham
- Rentals with a fireplace Windham
- Tiny house rentals Greene County
- Guesthouse rentals Greene County
- House rentals Greene County
- Townhouse rentals Greene County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom