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
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

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)
"Overall great experience. Very central location. Host lives in building, so is always available. They grow tomato's and cucumbers on the balcony that they invited us to "take as much as you want" My only discomfort with this place was the dust and dirty dishes. The people before us half-washed the things they used and the place seemed like it needed a pass with a vacuum cleaner. The floors were not very clean. In general, I greatly enjoyed my stay here."
United States
David
The price is NZ$449
includes taxes & fees
24 Sept - 25 Sept
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 NZ$877
includes taxes & fees
23 Sept - 24 Sept
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 NZ$959
includes taxes & fees
23 Sept - 24 Sept
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 NZ$938
includes taxes & fees
23 Sept - 24 Sept
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
The price is NZ$990
includes taxes & fees
23 Sept - 24 Sept
Large Chalet w/ Hot Tub, Fire Pit & 2 Living Rooms + Mins to Town & WMC
A pool area with a 'NO DIVING' sign, wooden benches, and stone walls.

6. 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 NZ$1,138
includes taxes & fees
23 Sept - 24 Sept
Charming 2-bedroom townhome in lovely Windham Mountain Village. Walk to skiing.
A fire pit with two chairs in a backyard.

7. NEW OUTDOOR HOT TUB!! 5 BEDROOM/3 BATH CHALET - HAUS WINDHAM

NEW OUTDOOR HOT TUB!! 5 BEDROOM/3 BATH CHALET - HAUS WINDHAM
Windham
The price is NZ$1,083
includes taxes & fees
23 Sept - 24 Sept
NEW OUTDOOR HOT TUB!! 5 BEDROOM/3 BATH CHALET - HAUS WINDHAM
A two-story house with a stone chimney, wooden deck, and a stone staircase leading to the entrance.

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

Luxury Windham Escape w/ Hot Tub, Views & Walk to Mountain
Windham
The price is NZ$1,928
includes taxes & fees
29 Sept - 30 Sept
Luxury Windham Escape w/ Hot Tub, Views & Walk to Mountain
Two wooden Adirondack chairs on a covered patio with a wooden fence in the background.

9. 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 NZ$645
includes taxes & fees
23 Sept - 24 Sept
Brand New 2 Bdr. Townhome Minutes from Windham Mtn
A cozy living room with a wooden ceiling, a sofa, a red chair, a fireplace, and a ceiling fan.

10. 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$764
includes taxes & fees
23 Sept - 24 Sept
Check our Reviews! Spectacular Views! King bed! Upgraded Baths n Kitchen!
A spacious kitchen with wooden cabinets, a stone fireplace, and large windows.

11. 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$774
includes taxes & fees
23 Sept - 24 Sept
Midnight Fox
A two-story wooden cabin with a deck and outdoor seating area.

12. Catskills Escape w/ Hot Tub & Fireplace

Catskills Escape w/ Hot Tub & Fireplace
Jewett
The price is NZ$1,131
includes taxes & fees
23 Sept - 24 Sept
Catskills Escape w/ Hot Tub & Fireplace
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.

13. Cozy Waterfall Oasis + Firepit

Cozy Waterfall Oasis + Firepit
East Durham
9.6 out of 10, Exceptional, (18 reviews)
"Everything was perfect!"
United States
Jen C.
The price is NZ$545
includes taxes & fees
23 Sept - 24 Sept
Cozy Waterfall Oasis + Firepit
A house with a fire pit and outdoor seating.

14. 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)
"House had everything, very clean, host very responsive, located close to everything. Great family vacation!"
United States
Jaylyn B.
The price is NZ$1,328
includes taxes & fees
20 Oct - 21 Oct
The Hensonville Honeypot - Hottub, Movie Theatre & Mountain Bikes!
A dining area with a wooden table, a woven pendant light, candles, a bottle of wine, and a vase with flowers.

15. 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 NZ$1,298
includes taxes & fees
23 Sept - 24 Sept
Hot Tub • Game Room • Fire Pit • 15 Private Acres
A wooden interior with a central fireplace, benches, and a window offering a forest view.

16. 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, (74 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 NZ$1,130
includes taxes & fees
1 Oct - 2 Oct
Mountain house with Scandinavian BBQ hut and Hot tub
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, (15 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 NZ$1,230
includes taxes & fees
23 Sept - 24 Sept
Catskill Mountain Hideaway with Amazing Hunter Mountain Views
A cozy living room with a white brick fireplace, a round table with a board of cured meats and cheese, two glasses of red wine, and a few potted plants.

18. Cute Cozy Catskill Escape

Cute Cozy Catskill Escape
Tannersville
10.0 out of 10, Exceptional, (1 review)
"This was the most stunning relaxing weekend me and my family had for years. clean and beautiful cozy house beautiful neighbourhood and some nice attractions in the area and most of all the best host you can ever hope for, from making sure everything is alright being responsive right away and what not he had no problem with anything we asked for. It’s a well maintained house and a brand new fridge freezer grill dishwasher dishes everything just perfect so if you are looking for a wonderful time...
United States
Benjamin S.
The price is NZ$1,379
includes taxes & fees
23 Sept - 24 Sept
Cute Cozy Catskill Escape
A rustic wooden interior with a sofa, a dining table, and a TV mounted on the wall.

19. 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 NZ$717
includes taxes & fees
27 Sept - 28 Sept
West Kill Barnhouse: Ski, Work & Unwind
A living room with a fireplace, a sliding glass door, and a rug.

20. Close to skiing and hiking, walk to main street

Close to skiing and hiking, walk to main street
Tannersville
9.2 out of 10, Wonderful, (15 reviews)
"Couldn't ask for a more perfect place to stay. Beautiful property, very quiet, and very comfy. You are on vacation but it feels like home. Definitely be staying here in the future!"
United States
Brandon M.
The price is NZ$725
includes taxes & fees
28 Sept - 29 Sept
Close to skiing and hiking, walk to main street
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

Jimmy OConnors Windham Mountain Inn

Jimmy OConnors Windham Mountain Inn

10/10 Excellent
"Cool little spot with the inn at the back of the property and the restaurant at the front. It’s been passed down through the family and I met the owner inside during a quick dinner, down to earth guy. The room is very vey clean and still sporting the original textures and fixtures, real retro feeling, I loved it."
Christopher 2-night trip
Posted less than an hour ago
Jimmy OConnors Windham Mountain Inn

Find out more about Windham

Windham Holiday Homes information

Number of reviews
3,415
Accommodation
731 Holiday Homes
Lowest Price
NZ$170
Highest Price
NZ$948

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