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

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Windham vacation 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
8.8 out of 10, Excellent, (65 reviews)
"Very nice hosts! Will come back again. Thanks very much!!"
United States
juneid a.
The price is SAR 413
SAR 734 total
includes taxes & fees
2 Nov - 3 Nov
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
9.0 out of 10, Wonderful, (9 reviews)
"We loved ,.. place was very clean and organized "
United States
Cristina L.
The price is SAR 1,209
SAR 2,566 total
includes taxes & fees
24 Nov - 25 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 SAR 653
SAR 1,893 total
includes taxes & fees
27 Oct - 28 Oct
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.
Pines Vignette • Modern 3BR Home in Windham
A large, two-story house with a stone facade, a wooden deck, and a clear sky.

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 SAR 746
SAR 2,796 total
includes taxes & fees
26 Oct - 27 Oct
Large Chalet w/ Hot Tub, Fire Pit & 2 Living Rooms + Mins to Town & WMC
A fire pit with two chairs in a backyard.

6. 5 Bedroom/3 Bath Chalet | Haus Windham

5 Bedroom/3 Bath Chalet | Haus Windham
Windham
The price is SAR 1,310
SAR 2,338 total
includes taxes & fees
26 Oct - 27 Oct
5 Bedroom/3 Bath Chalet | Haus Windham
A two-story house with a stone chimney, wooden balconies, and a stone facade.

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

Luxury Windham Escape w/ Hot Tub, Views & Walk to Mountain
Windham
Luxury Windham Escape w/ Hot Tub, Views & Walk to Mountain
A living room with a sectional sofa, a wooden coffee table, and a view through large arched windows to an outdoor deck.

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

Luxury Windham Retreat w/ Hot Tub & Fireplace, Mins to Slopes
Windham
Luxury Windham Retreat w/ Hot Tub & Fireplace, Mins to Slopes
Entryway area

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.
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.

10. 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, (12 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 SAR 676
SAR 1,382 total
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.

11. 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 Hensonville Honeypot - Hottub, Movie Theatre & Mountain Bikes!
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.
Midnight Fox
A wooden cabin with a deck, outdoor seating, and a staircase.

13. Catskills Escape w/ Hot Tub & Fireplace

Catskills Escape w/ Hot Tub & Fireplace
Jewett
Catskills Escape w/ Hot Tub & Fireplace
A building with a red roof, surrounded by a grassy area with yellow flowers and a large tree.

14. 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, (97 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 SAR 515
SAR 1,412 total
includes taxes & fees
1 Nov - 2 Nov
2BR Mountain View Home with Pool & 3 mins to Ski Slopes
A modern kitchen with a stainless steel refrigerator, a dining area with a table and chairs, and a living room with a sofa and a lamp.

15. 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 SAR 523
SAR 1,233 total
includes taxes & fees
26 Oct - 27 Oct
Cozy Waterfall Oasis + Firepit
A rustic wooden interior with a sofa, a dining table, and a TV mounted on the wall.

16. 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.
West Kill Barnhouse: Ski, Work & Unwind
A living room with a fireplace, a television, a sofa, and a dining area with chairs.

17. Town Home near Hunter Mntn

Town Home near Hunter Mntn
Tannersville
9.4 out of 10, Exceptional, (59 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 SAR 533
SAR 1,731 total
includes taxes & fees
1 Nov - 2 Nov
Town Home near Hunter Mntn
A modern kitchen with wooden cabinets, a central island, and a dining area with a high table and chairs.

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 SAR 507
SAR 4,194 total
includes taxes & fees
1 Nov - 2 Nov
The Homestead at Carter Bridge Estate
A cozy living room with a wooden ceiling, a sofa, a red chair, a fireplace, and a ceiling fan.

19. 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 SAR 822
SAR 1,686 total
includes taxes & fees
7 Nov - 8 Nov
Check our Reviews! Spectacular Views! King bed! Upgraded Baths n Kitchen!
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.
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Top Windham Hotel Reviews

Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG

10/10 Excellent
"The room was very clean and the staff were very courteous and helpful."
Jacqueline 1-night trip
Posted less than an hour ago
Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG