A winding road through a forest with autumn foliage, a rocky cliff on the right, and a mountain in the background.

Holiday Homes in Windham

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
31 July - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Windham holiday homes

Exterior

TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores

TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Windham
9.0 out of 10, Wonderful, (61 reviews)
"Good size space in a great location. Would definitely stay here again "
United States
Michael C.
The price is AU$321
includes taxes & fees
10 Aug - 11 Aug
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Exterior

Pines Vignette • Modern 3BR Home in Windham

Pines Vignette • Modern 3BR Home in Windham
Windham
10.0 out of 10, Exceptional, (2 reviews)
"House is cozy and has everything you need. We enjoyed our stay."
United States
William H.
The price is AU$751
includes taxes & fees
21 July - 22 July
Pines Vignette • Modern 3BR Home in Windham
Dining

2 Min Walk to Windham Town | Hot Tub | Fire Pit

2 Min Walk to Windham Town | Hot Tub | Fire Pit
Windham
10.0 out of 10, Exceptional, (3 reviews)
"Great location, perfect layout and responsive host! Thanks for hosting - would gladly stay again. "
United States
Melissa R.
The price is AU$829
includes taxes & fees
22 July - 23 July
2 Min Walk to Windham Town | Hot Tub | Fire Pit
Exterior

Hot Tub, Fire pit, Fireplace - Large Chalet Just Minutes to Town + WMC

Hot Tub, Fire pit, Fireplace - Large Chalet Just Minutes to Town + WMC
Windham
The price is AU$868
includes taxes & fees
29 July - 30 July
Hot Tub, Fire pit, Fireplace - Large Chalet Just Minutes to Town + WMC
TV, fireplace

Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome

Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
Windham
9.6 out of 10, Exceptional, (7 reviews)
"We loved ,.. place was very clean and organized "
United States
Cristina L.
The price is AU$803
includes taxes & fees
19 July - 20 July
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
Indoor pool, a heated pool

Charming 2-bedroom townhome in lovely Windham Mountain Village. Walk to skiing.

Charming 2-bedroom townhome in lovely Windham Mountain Village. Walk to skiing.
Windham
10.0 out of 10, Exceptional, (1 review)
"Host had an amazing response time. Very easy to talk with via email. She had very clear and easy instructions on check in and check out. The place had lots of bedding, it was warm and inviting, had everything we needed. My daughter thought the “balcony” on the second floor which over looked the kitchen was cool! "
United States
Soonae S.
The price is AU$979
includes taxes & fees
22 July - 23 July
Charming 2-bedroom townhome in lovely Windham Mountain Village. Walk to skiing.
TV, fireplace

Ask about Spring Specials!

Ask about Spring Specials!
Windham
10.0 out of 10, Exceptional, (4 reviews)
"We had a great three day getaway in Windham. The house was a great spot for a ski getaway in the mountains. Nice open floor plan and every bedroom had a bathroom which was great"
United States
Jim V.
The price is AU$1,225
includes taxes & fees
22 July - 23 July
Ask about Spring Specials!
Coffee/tea maker, microwave, oven, stovetop

Ask about Spring Specials!

Ask about Spring Specials!
Windham
10.0 out of 10, Exceptional, (2 reviews)
"I really enjoyed my time here. The house was comfortable, modern and well taken care of, and the property it was on was beautiful. Good access to town as well, and the full kitchen was well appointed. I had a really relaxing weekend, I'd book this again."
United States
Robert G.
The price is AU$1,225
includes taxes & fees
22 July - 23 July
Ask about Spring Specials!
TV, fireplace

Ask about Spring Specials!

Ask about Spring Specials!
Windham
10.0 out of 10, Exceptional, (1 review)
"We had an amazing time in this magnificent, beautiful home. Our family books ski trips throughout the northeast twice a year as a group of 10 for the past 10 years. This house has by far ranked #1 as the best house we have stayed in. 10 minutes away from the mountain (Windham). 4 large sized bedrooms each with their own large bathrooms. A beautiful dream kitchen with all the essentials. We did plenty of cooking. We loved the open layout of the home. We will definitely be back for sure. "
United States
Anonymous traveller
The price is AU$1,225
includes taxes & fees
22 July - 23 July
Ask about Spring Specials!
Exterior

Modern Luxurious Cabin, Catskills - The Tiny Nook

Modern Luxurious Cabin, Catskills - The Tiny Nook
Catskill
10.0 out of 10, Exceptional, (11 reviews)
"We had an excellent experience. The place was wonderful. A real place to disconnect from everything. We Highly recommend it."
United States
Saul
The price is AU$489
includes taxes & fees
20 July - 21 July
Modern Luxurious Cabin, Catskills - The Tiny Nook
Property grounds

Brand New 2 Bdr. Townhome Minutes from Windham Mtn

Brand New 2 Bdr. Townhome Minutes from Windham Mtn
Hensonville
10.0 out of 10, Exceptional, (10 reviews)
"This is a very cute, very clean condo near Windham. Perfect for our family of 4. Would definitely stay again. "
United States
Kimberly K.
The price is AU$518
includes taxes & fees
22 July - 23 July
Brand New 2 Bdr. Townhome Minutes from Windham Mtn
Smart TV, fireplace

Cozy Waterfall Oasis + Firepit

Cozy Waterfall Oasis + Firepit
East Durham
9.4 out of 10, Exceptional, (16 reviews)
"Everything was perfect!"
United States
Jen C.
The price is AU$536
includes taxes & fees
19 July - 20 July
Cozy Waterfall Oasis + Firepit
TV

Cabin Oasis near Town

Cabin Oasis near Town
Catskill
The price is AU$396
includes taxes & fees
22 July - 23 July
Cabin Oasis near Town
Exterior

Cozy Country Farmhouse Along the Catskill Scenic Trail

Cozy Country Farmhouse Along the Catskill Scenic Trail
Hobart
10.0 out of 10, Exceptional, (128 reviews)
"We loved our stay. The house was clean and generously stocked."
United States
Amy W.
The price is AU$479
includes taxes & fees
11 Aug - 12 Aug
Cozy Country Farmhouse Along the Catskill Scenic Trail
Property grounds

Starlit Geodesic Dome Haven Overlooking a Mountain River in New York’s Catskills

Starlit Geodesic Dome Haven Overlooking a Mountain River in New York’s Catskills
Gilboa
The price is AU$327
includes taxes & fees
21 July - 22 July
Starlit Geodesic Dome Haven Overlooking a Mountain River in New York’s Catskills
Fridge, oven, stovetop, dishwasher

Cozy Catskill Escape

Cozy Catskill Escape
Catskill
The price is AU$403
includes taxes & fees
21 July - 22 July
Cozy Catskill Escape
Interior

Mountain retreat/Hot Tub/Ski/Hike/Water Park/WIFI/Fire Pit

Mountain retreat/Hot Tub/Ski/Hike/Water Park/WIFI/Fire Pit
Durham
10.0 out of 10, Exceptional, (3 reviews)
"Was close to where we were attending a wedding and big enough to house us all!"
United States
Paul m.
The price is AU$687
includes taxes & fees
20 July - 21 July
Mountain retreat/Hot Tub/Ski/Hike/Water Park/WIFI/Fire Pit
Exterior

Modern cabin retreat

Modern cabin retreat
Catskill
The price is AU$412
includes taxes & fees
21 July - 22 July
Modern cabin retreat
Smart TV, books, stereo, computer monitors

Upgraded! Perfect location seconds from Hunter Mtn! Incredible views! King bed!

Upgraded! Perfect location seconds from Hunter Mtn! Incredible views! King bed!
Hunter
9.8 out of 10, Exceptional, (18 reviews)
"Nice home, spacious, and conveniently located minutes from Hunter. I would stay here again. "
United States
Jim D.
The price is AU$624
includes taxes & fees
21 July - 22 July
Upgraded! Perfect location seconds from Hunter Mtn! Incredible views! King bed!
Interior

Midnight Fox

Midnight Fox
Hunter
10.0 out of 10, Exceptional, (12 reviews)
"House was very clean and beds were super comfy after a day of skiing ! "
United States
Caroline I.
The price is AU$619
includes taxes & fees
22 July - 23 July
Midnight Fox
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.
View all properties
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
"Clean room"
Slavin 2-night trip
Posted 8 hours ago
Hotel Vienna

Find out more about Windham

Windham Holiday Homes information

Number of reviews
218
Accommodation
740 Holiday Homes
Lowest Price
AU$321
Highest Price
AU$1,225