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
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Windham holiday homes

Exterior

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, (62 reviews)
"Good size space in a great location. Would definitely stay here again "
United States
Michael C.
The price is £163
includes taxes & fees
12 Aug - 13 Aug
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Exterior

2. 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 £413
includes taxes & fees
1 Sept - 2 Sept
Hot Tub, Fire pit, Fireplace - Large Chalet Just Minutes to Town + WMC
Dining

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 £420
includes taxes & fees
18 Aug - 19 Aug
2 Min Walk to Windham Town | Hot Tub | Fire Pit
Exterior

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 £372
includes taxes & fees
9 Sept - 10 Sept
Pines Vignette • Modern 3BR Home in Windham
TV, fireplace

5. 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 £438
includes taxes & fees
12 Aug - 13 Aug
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
Outdoor dining

6. 'The Mountain House:' Windham Retreat w/ Hot Tub!

'The Mountain House:' Windham Retreat w/ Hot Tub!
Windham
10.0 out of 10, Exceptional, (36 reviews)
"Great stay Very comfortable "
United States
Teresa G.
The price is £603
includes taxes & fees
27 Aug - 28 Aug
'The Mountain House:' Windham Retreat w/ Hot Tub!
Indoor pool, a heated pool

7. 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 £499
includes taxes & fees
23 Aug - 24 Aug
Charming 2-bedroom townhome in lovely Windham Mountain Village. Walk to skiing.
Property grounds

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, (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 £267
includes taxes & fees
12 Aug - 13 Aug
Brand New 2 Bdr. Townhome Minutes from Windham Mtn
Smart TV, fireplace

9. Cozy Waterfall Oasis + Firepit

Cozy Waterfall Oasis + Firepit
East Durham
9.6 out of 10, Exceptional, (17 reviews)
"Everything was perfect!"
United States
Jen C.
The price is £242
includes taxes & fees
12 Aug - 13 Aug
Cozy Waterfall Oasis + Firepit
Children’s area

10. Cozy 2-bedroom house in Haines Falls near Katterskill falls .

Cozy 2-bedroom house in Haines Falls near Katterskill falls .
Haines Falls
10.0 out of 10, Exceptional, (1 review)
"House was clean and well kept, perfect for our family weekend trip!"
United States
Edward C.
The price is £275
includes taxes & fees
12 Aug - 13 Aug
Cozy 2-bedroom house in Haines Falls near Katterskill falls .
Smart TV, books, stereo, computer monitors

11. 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 £323
includes taxes & fees
12 Aug - 13 Aug
Upgraded! Perfect location seconds from Hunter Mtn! Incredible views! King bed!
Interior

12. 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 £269
includes taxes & fees
12 Aug - 13 Aug
West Kill Barnhouse: Ski, Work & Unwind
Interior

13. 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 £331
includes taxes & fees
17 Aug - 18 Aug
Midnight Fox
Sauna

14. 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, (73 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 £486
includes taxes & fees
12 Aug - 13 Aug
Mountain house with Scandinavian BBQ hut and Hot tub
Interior

15. Entire Renovated Country House, Sleeps 7, Pets, Creek Across the Street

Entire Renovated Country House, Sleeps 7, Pets, Creek Across the Street
West Kill
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful setting. Great light throughout the house. Convenient to the ski mountains"
United States
Timothy M.
The price is £318
includes taxes & fees
16 Aug - 17 Aug
Entire Renovated Country House, Sleeps 7, Pets, Creek Across the Street
Exterior

16. 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 £321
includes taxes & fees
9 Sept - 10 Sept
Large Cook's Kitchen; 1st Fl Bedroom w/ Ensuite; 10-Min to downtown Fleischmanns
Terrace/patio

17. 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 £161
includes taxes & fees
19 Aug - 20 Aug
Starlit Geodesic Dome Haven Overlooking a Mountain River in New York’s Catskills
Smart TV, fireplace, books

18. Catskill Mountain Hideaway with Amazing Hunter Mountain Views

Catskill Mountain Hideaway with Amazing Hunter Mountain Views
Hunter
10.0 out of 10, Exceptional, (14 reviews)
"Very clean and comfy place to stay. Communication with owner is quick and easy. Highly recommendations "
United States
ching yi t.
The price is £501
includes taxes & fees
23 Aug - 24 Aug
Catskill Mountain Hideaway with Amazing Hunter Mountain Views
Interior

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, (6 reviews)
"The property is located on incredible Landfield....the view is spectacular and everything around is nature."
United States
NANCY
The price is £522
includes taxes & fees
8 Sept - 9 Sept
Spacious 5 BR w/Mountaintop Views-2 Min to Hunter
Dining

20. Hot Tub • Pool Table • Fire Pit • Game Room •Views - Holiday Home

Hot Tub • Pool Table • Fire Pit • Game Room •Views - Holiday Home
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 £625
includes taxes & fees
1 Sept - 2 Sept
Hot Tub • Pool Table • Fire Pit • Game Room •Views - Holiday Home
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

Hotel Vienna

Hotel Vienna

10/10 Excellent
"Great weekend visit at Hotel Vienna with our 2 small dogs! Check in and check out were super easy, staff was helpful and accommodating, and the property was really quiet, very clean and super well maintained. The bathrooms were obviously recently renovated and very tastefully done, the bed was firm and linens soft and comfy. Breakfast was pastries, cereal, and yogurt; all were high quality, fresh and delicious. Cappuccino and tea were lovely. Shower pressure could have been a bit better, but that was literally the only downside. We did not have a chance to use the pool, but it looked very clean, located in a nice, stand-alone building with windows and skylights. Barrel sauna is just outside on the deck, and both are is surrounded by beautiful landscaping. The main building also has two sunny, well furnished decks, and there are fire pits with Adirondack chairs located about the property, and there's direct access to the Windham Path and dog park. Sad I missed the free Saturday morning yoga, but I'll definitely try to make it next time. All in all, this hotel was perfect, peaceful, and we'll definitely be back to explore all the things we missed!"
Alicia 2-night trip
Posted 1 day ago
Hotel Vienna

Find out more about Windham

Windham Holiday Homes information

Number of reviews
281
Accommodation
741 Holiday Homes
Lowest Price
£161
Highest Price
£625