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Check prices for these dates

Our top choices for Windham holiday homes

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
8.8 out of 10, Excellent, (66 reviews)
"The pictures are not accurate. The two full and one twin bed are in one room upstairs, they are not separated as pictures would lead you to believe. Then three twins are in the living room with the couch, next to the dining room table and kitchen. The unit was dusty and not swept clean. There were dead bugs on the floor and party poppers from previous guest. I have never experienced something like this with Expedia, this was a zero star experience honestly."
United States
April
The price is £142
includes taxes & fees
12 Nov - 13 Nov
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores

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

Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
Windham
9.0 out of 10, Wonderful, (9 reviews)
"We loved ,.. place was very clean and organized "
United States
Cristina L.
The price is £350
includes taxes & fees
11 Nov - 12 Nov
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome

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 £383
includes taxes & fees
11 Nov - 12 Nov
2 Min Walk to Windham Town | Hot Tub | Fire Pit

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 £381
includes taxes & fees
11 Nov - 12 Nov
Pines Vignette • Modern 3BR Home in Windham

5. Large Chalet w/ Hot Tub, Fire Pit & 2 Living Rooms + Mins to Town & WMC

Large Chalet w/ Hot Tub, Fire Pit & 2 Living Rooms + Mins to Town & WMC
Windham
10.0 out of 10, Exceptional, (1 review)
"My stay was very short but we maximized our time by enjoying the properties endless offerings. Lots of things to do and board games were available. Plenty of room and beds every one. View from jacuzzi was phenomenal to see the stars at night. I’d recommend definitely and will revisit during winter"
United States
Lobid C.
The price is £547
includes taxes & fees
11 Nov - 12 Nov
Large Chalet w/ Hot Tub, Fire Pit & 2 Living Rooms + Mins to Town & WMC

6. Luxury Windham Escape w/ Hot Tub, Ski on/off one block from Mountain

Luxury Windham Escape w/ Hot Tub, Ski on/off one block from Mountain
Windham
The price is £729
includes taxes & fees
12 Nov - 13 Nov
Luxury Windham Escape w/ Hot Tub, Ski on/off one block from Mountain

7. 5BR Chalet Sleeps 12 with Jacuzzi, Sauna and Gym, 3 Min to Windham Mtn

5BR Chalet Sleeps 12 with Jacuzzi, Sauna and Gym, 3 Min to Windham Mtn
Windham
The price is £456
includes taxes & fees
30 Nov - 1 Dec
5BR Chalet Sleeps 12 with Jacuzzi, Sauna and Gym, 3 Min to Windham Mtn

8. Luxury Windham Retreat w/ Hot Tub & Fireplace, Mins to Slopes

Luxury Windham Retreat w/ Hot Tub & Fireplace, Mins to Slopes
Windham
The price is £664
includes taxes & fees
11 Nov - 12 Nov
Luxury Windham Retreat w/ Hot Tub & Fireplace, Mins to Slopes

9. 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 £357
includes taxes & fees
11 Nov - 12 Nov
Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!

10. 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 £552
includes taxes & fees
16 Nov - 17 Nov
The Hensonville Honeypot - Hottub, Movie Theatre & Mountain Bikes!

11. 2BR Mountain View Home with Pool & 3 mins to Ski Slopes

2BR Mountain View Home with Pool & 3 mins to Ski Slopes
Tannersville
9.8 out of 10, Exceptional, (98 reviews)
"Great location, house is a bit run down. If you’re there just for skiing, this would be a great home."
United States
Murodjon R.
The price is £268
includes taxes & fees
15 Nov - 16 Nov
2BR Mountain View Home with Pool & 3 mins to Ski Slopes

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 £317
includes taxes & fees
11 Nov - 12 Nov
Midnight Fox

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 £501
includes taxes & fees
15 Nov - 16 Nov
Catskill Mountain Hideaway with Amazing Hunter Mountain Views

14. Catskills Escape w/ Hot Tub & Fireplace

Catskills Escape w/ Hot Tub & Fireplace
Jewett
The price is £579
includes taxes & fees
15 Nov - 16 Nov
Catskills Escape w/ Hot Tub & Fireplace

15. Town Home near Hunter Mntn

Town Home near Hunter Mntn
Tannersville
9.4 out of 10, Exceptional, (60 reviews)
"As a family we had a beautiful time together visiting the sights and walking out the skirts of the mountains."
United States
Guadalupe G.
The price is £339
includes taxes & fees
11 Nov - 12 Nov
Town Home near Hunter Mntn

16. Lovely en-suite with private entrance.

Lovely en-suite with private entrance.
East Jewett
The price is £187
includes taxes & fees
23 Nov - 24 Nov
Lovely en-suite with private entrance.

17. 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 £313
includes taxes & fees
16 Nov - 17 Nov
Check our Reviews! Spectacular Views! King bed! Upgraded Baths n Kitchen!

18. Cozy Waterfall Oasis + Firepit

Cozy Waterfall Oasis + Firepit
East Durham
9.6 out of 10, Exceptional, (19 reviews)
"Great property! Spacious enough for 4 adults, lovely porch, good wifi, clear instructions for check in and out and a responsive host!"
United States
Holly C.
The price is £239
includes taxes & fees
15 Nov - 16 Nov
Cozy Waterfall Oasis + Firepit

19. 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, (9 reviews)
"Great time had by all of us! House is perfect for several families and so much to do in the area. Would definitely stay again! Owners were very easy to access for questions."
United States
Michelle D.
The price is £522
includes taxes & fees
1 Dec - 2 Dec
Spacious 5 BR w/Mountaintop Views-2 Min to Hunter

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 £568
includes taxes & fees
11 Nov - 12 Nov
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.

Learn more about Windham

Nestled in the Catskills, this mountain town transforms from a powdery ski paradise to a lush hiking haven with seasons. Visit Windham Mountain for thrilling slopes in winter or explore the scenic Rail Trail when summer's wildflowers frame perfect mountain views.

Two skiers on a snowy slope with a valley and mountains in the background.

Top reviews in Windham