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
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Windham holiday homes

A two-story building with large windows and a storefront.

1. 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, (64 reviews)
"Very nice hosts! Will come back again. Thanks very much!!"
United States
juneid a.
The price is AU$333
includes taxes & fees
18 Oct - 19 Oct
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
A spacious living area with a wooden dining table, a sofa, a fireplace, and a view of the outdoors.

2. 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, (8 reviews)
"We loved ,.. place was very clean and organized "
United States
Cristina L.
The price is AU$677
includes taxes & fees
3 Nov - 4 Nov
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
A dining area with a wooden table, six chairs, a chandelier, and a wall-mounted shelf.

3. 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$762
includes taxes & fees
3 Nov - 4 Nov
2 Min Walk to Windham Town | Hot Tub | Fire Pit
A two-story cabin with a balcony and a chimney, surrounded by a snowy forest.

4. 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$761
includes taxes & fees
28 Oct - 29 Oct
Pines Vignette • Modern 3BR Home in Windham
A fire pit with two chairs in a backyard.

5. Private 5BR Chalet Sleeping 12 with Fire Pit near Windham Mtn

Private 5BR Chalet Sleeping 12 with Fire Pit near Windham Mtn
Windham
The price is AU$997
includes taxes & fees
28 Oct - 29 Oct
Private 5BR Chalet Sleeping 12 with Fire Pit near Windham Mtn
A hot tub with a fire pit, surrounded by Adirondack chairs, and string lights.

6. Luxury Windham Escape w/ Hot Tub, Views & Walk to Mountain

Luxury Windham Escape w/ Hot Tub, Views & Walk to Mountain
Windham
The price is AU$1,516
includes taxes & fees
20 Oct - 21 Oct
Luxury Windham Escape w/ Hot Tub, Views & Walk to Mountain
Entryway area

7. Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!

Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!
Ashland
9.2 out of 10, Wonderful, (5 reviews)
"Great place to stay very accommodating more than expected "
United States
Julia M.
The price is AU$772
includes taxes & fees
28 Oct - 29 Oct
Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!
Two wooden Adirondack chairs on a covered patio with a wooden fence in the background.

8. 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, (11 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$513
includes taxes & fees
26 Oct - 27 Oct
Brand New 2 Bdr. Townhome Minutes from Windham Mtn
A house with a fire pit and outdoor seating.

9. The Hensonville Honeypot - Hottub, Movie Theatre & Mountain Bikes!

The Hensonville Honeypot - Hottub, Movie Theatre & Mountain Bikes!
Hensonville
10.0 out of 10, Exceptional, (8 reviews)
"Fantastic property. Especially good for families or groups. So much to do right on property, almost no need to leave. Place was exactly as described."
United States
David H.
The price is AU$1,526
includes taxes & fees
12 Nov - 13 Nov
The Hensonville Honeypot - Hottub, Movie Theatre & Mountain Bikes!
A wooden interior with a central fireplace, benches, and a window offering a forest view.

10. Mountain house with Scandinavian BBQ hut and Hot tub

Mountain house with Scandinavian BBQ hut and Hot tub
Jewett
10.0 out of 10, Exceptional, (76 reviews)
"Beautiful home, comfortable bedding, great amenities, great communication with host, overall lovely property. We loved the jacuzzi, bbq hut & she shed. "
United States
Despina M.
The price is AU$977
includes taxes & fees
12 Nov - 13 Nov
Mountain house with Scandinavian BBQ hut and Hot tub
A bedroom with a bed, wooden dresser, ceiling fan, framed pictures, and a view into the kitchen.

11. Catskills Escape w/ Hot Tub & Fireplace

Catskills Escape w/ Hot Tub & Fireplace
Jewett
The price is AU$902
includes taxes & fees
28 Oct - 29 Oct
Catskills Escape w/ Hot Tub & Fireplace
A spacious kitchen with wooden cabinets, a stone fireplace, and large windows.

12. Midnight Fox

Midnight Fox
Hunter
10.0 out of 10, Exceptional, (15 reviews)
"House was very clean and beds were super comfy after a day of skiing ! "
United States
Caroline I.
The price is AU$633
includes taxes & fees
28 Oct - 29 Oct
Midnight Fox
A spacious living area with a large window, a ceiling fan, and a dining table set for four.

13. Catskill Mountain Hideaway with Amazing Hunter Mountain Views

Catskill Mountain Hideaway with Amazing Hunter Mountain Views
Hunter
10.0 out of 10, Exceptional, (16 reviews)
"The location was perfect, and the view of Hunter Mountain was beautiful. Our stay was enjoyable for travelers of all ages."
United States
Allyson R.
The price is AU$1,029
includes taxes & fees
20 Oct - 21 Oct
Catskill Mountain Hideaway with Amazing Hunter Mountain Views
A modern bathroom with a glass shower enclosure, a toilet, and a sink.

14. Cozy Waterfall Oasis + Firepit

Cozy Waterfall Oasis + Firepit
East Durham
9.6 out of 10, Exceptional, (19 reviews)
"Everything was perfect!"
United States
Jen C.
The price is AU$460
includes taxes & fees
15 Oct - 16 Oct
Cozy Waterfall Oasis + Firepit
A rustic wooden interior with a sofa, a dining table, and a TV mounted on the wall.

15. West Kill Barnhouse: Ski, Work & Unwind

West Kill Barnhouse: Ski, Work & Unwind
West Kill
10.0 out of 10, Exceptional, (18 reviews)
"Great stay"
United States
Vijay S.
The price is AU$575
includes taxes & fees
18 Oct - 19 Oct
West Kill Barnhouse: Ski, Work & Unwind
A cozy living room with a wooden ceiling, a sofa, a red chair, a fireplace, and a ceiling fan.

16. Check our Reviews! Spectacular Views! King bed! Upgraded Baths n Kitchen!

Check our Reviews! Spectacular Views! King bed! Upgraded Baths n Kitchen!
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$630
includes taxes & fees
23 Oct - 24 Oct
Check our Reviews! Spectacular Views! King bed! Upgraded Baths n Kitchen!
A round table with a candle, a book, and a vase with dried flowers.

17. Spacious 5 BR w/Mountaintop Views-2 Min to Hunter

Spacious 5 BR w/Mountaintop Views-2 Min to Hunter
Tannersville
10.0 out of 10, Exceptional, (8 reviews)
"The property is located on incredible Landfield....the view is spectacular and everything around is nature."
United States
NANCY
The price is AU$1,025
includes taxes & fees
21 Oct - 22 Oct
Spacious 5 BR w/Mountaintop Views-2 Min to Hunter
A two-story house with a patio area, outdoor seating, and a small tree.

18. The Homestead at Carter Bridge Estate

The Homestead at Carter Bridge Estate
Freehold
10.0 out of 10, Exceptional, (3 reviews)
"This was an excellent home that we stayed in total of six adults. We went to the Gray Fox music festival and it was very close by. The property manager was very responsive and communicative. Highly recommend this house."
United States
ELIZABETH
The price is AU$1,616
includes taxes & fees
18 Oct - 19 Oct
The Homestead at Carter Bridge Estate
A wooden cabin with a porch, two chairs, and a table.

19. Large Cook's Kitchen; 1st Fl Bedroom w/ Ensuite; 10-Min to downtown Fleischmanns

Large Cook's Kitchen; 1st Fl Bedroom w/ Ensuite; 10-Min to downtown Fleischmanns
Halcott Center
10.0 out of 10, Exceptional, (6 reviews)
"Everything was perfect during my stay. The service was excellent, and everything went very smoothly. I’m really happy with the overall experience and would highly recommend it to anyone."
United States
Hnin
The price is AU$605
includes taxes & fees
8 Nov - 9 Nov
Large Cook's Kitchen; 1st Fl Bedroom w/ Ensuite; 10-Min to downtown Fleischmanns
A dining area with a wooden table, a woven pendant light, candles, a bottle of wine, and a vase with flowers.

20. Hot Tub • Game Room • Fire Pit • 15 Private Acres

Hot Tub • Game Room • Fire Pit • 15 Private Acres
East Jewett
10.0 out of 10, Exceptional, (7 reviews)
"My family and I had a wonderful experience at this property. The house was clean, nicely decorated and had everything you need to feel at home! Jeff, the host , was so helpful and accommodating. We will definitely be back!"
United States
Beth C.
The price is AU$1,412
includes taxes & fees
28 Oct - 29 Oct
Hot Tub • Game Room • Fire Pit • 15 Private Acres
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

The Haüs Windham

The Haüs Windham

10/10 Excellent
"Just go to this location"
thespena 1-night trip
Posted 1 hour ago
The Haüs Windham

Find out more about Windham

Windham Holiday Homes information

Number of reviews
230
Accommodation
726 Holiday Homes
Lowest Price
AU$333
Highest Price
AU$1,616