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

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 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
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 NZ$330
includes taxes & fees
11 Nov - 12 Nov
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
A dining area with a wooden table, six chairs, a chandelier, and a wall-mounted shelf.

2. 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 NZ$988
includes taxes & fees
1 Dec - 2 Dec
2 Min Walk to Windham Town | Hot Tub | Fire Pit
A spacious living area with a wooden dining table, a sofa, a fireplace, and a view of the outdoors.

3. 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 NZ$909
includes taxes & fees
9 Nov - 10 Nov
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
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 NZ$919
includes taxes & fees
10 Nov - 11 Nov
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 NZ$1,286
includes taxes & fees
1 Dec - 2 Dec
Large Chalet w/ Hot Tub, Fire Pit & 2 Living Rooms + Mins to Town & WMC
A spacious living room with a fireplace, a large sofa, a coffee table, and a TV.

6. 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 NZ$1,082
includes taxes & fees
1 Dec - 2 Dec
5BR Chalet Sleeps 12 with Jacuzzi, Sauna and Gym, 3 Min to Windham Mtn
A two-story house with a stone chimney, wooden deck, and a stone staircase leading to the entrance.

7. 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 NZ$1,974
includes taxes & fees
19 Nov - 20 Nov
Luxury Windham Escape w/ Hot Tub, Ski on/off one block from 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
The price is NZ$1,556
includes taxes & fees
19 Nov - 20 Nov
Luxury Windham Retreat w/ Hot Tub & Fireplace, Mins to Slopes
A deck with a table and chairs, overlooking a forested hillside.

9. Windham Mountain Chalet - Hot Tub, Sauna, Gym & Game Room, Sleeps 10

Windham Mountain Chalet - Hot Tub, Sauna, Gym & Game Room, Sleeps 10
Windham
10.0 out of 10, Exceptional, (3 reviews)
"This was a gem of a property. Super clean and cozy. Fantastic amenities! The host was always responsive. We plan on renting this property again in the future. "
United States
Derrick S.
The price is NZ$1,859
includes taxes & fees
7 Nov - 8 Nov
Windham Mountain Chalet - Hot Tub, Sauna, Gym & Game Room, Sleeps 10
Entryway area

10. 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 NZ$924
includes taxes & fees
19 Nov - 20 Nov
Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!
A blue house with a deck, outdoor seating, and a hot tub.

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

'The Mountain House:' Windham Retreat w/ Hot Tub!
Windham
10.0 out of 10, Exceptional, (39 reviews)
"Great stay Very comfortable "
United States
Teresa G.
'The Mountain House:' Windham Retreat w/ Hot Tub!
A house with a fire pit and outdoor seating.

12. 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 NZ$1,358
includes taxes & fees
16 Nov - 17 Nov
The Hensonville Honeypot - Hottub, Movie Theatre & Mountain Bikes!
A spacious kitchen with wooden cabinets, a stone fireplace, and large windows.

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 NZ$751
includes taxes & fees
19 Nov - 20 Nov
Midnight Fox
A living room with a fireplace, a television, a sofa, and a dining area with chairs.

14. 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 NZ$866
includes taxes & fees
20 Nov - 21 Nov
Town Home near Hunter Mntn
A building with a red roof, surrounded by a grassy area with yellow flowers and a large tree.

15. 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 NZ$661
includes taxes & fees
19 Nov - 20 Nov
2BR Mountain View Home with Pool & 3 mins to Ski Slopes
A spacious dining area with a high ceiling, exposed wooden beams, and hanging light fixtures.

16. Catskills Escape w/ Hot Tub & Fireplace

Catskills Escape w/ Hot Tub & Fireplace
Jewett
The price is NZ$1,344
includes taxes & fees
8 Nov - 9 Nov
Catskills Escape w/ Hot Tub & Fireplace
A spacious living area with a large window, a ceiling fan, and a dining table set for four.

17. 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 NZ$1,159
includes taxes & fees
8 Nov - 9 Nov
Catskill Mountain Hideaway with Amazing Hunter Mountain Views
A cozy living room with a wooden ceiling, a sofa, a red chair, a fireplace, and a ceiling fan.

18. 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 NZ$716
includes taxes & fees
7 Nov - 8 Nov
Check our Reviews! Spectacular Views! King bed! Upgraded Baths n Kitchen!
A small house with a porch, a table, and two chairs.

19. Lovely en-suite with private entrance.

Lovely en-suite with private entrance.
East Jewett
The price is NZ$432
includes taxes & fees
19 Nov - 20 Nov
Lovely en-suite with private entrance.
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.

20. 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 NZ$568
includes taxes & fees
8 Nov - 9 Nov
Cozy Waterfall Oasis + Firepit
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

Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark

10/10 Excellent
"Pleasant stay. Would definitely stay there again."
patricia 1-night trip
Posted 10 hours ago
Hunter Lodge, a Bluebird by Lark

Find out more about Windham

Windham Holiday Homes information

Number of reviews
214
Accommodation
721 Holiday Homes
Lowest Price
NZ$330
Highest Price
NZ$1,974

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