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

Windham Vacation Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Windham vacation rentals

A two-story building with large windows and a storefront.

1. Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter

Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
Windham
9.2 out of 10, Wonderful, (45 reviews)
"Perfect stay cozy and convenient "
United States
Ahmad O.
The price is AED 331
AED 555 total
includes taxes & fees
4 Oct - 5 Oct
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
A two-story building with large windows and a storefront.

2. 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 AED 588
AED 912 total
includes taxes & fees
29 Sep - 30 Sep
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
A bedroom with a wooden ceiling, a large window, a bed, and a bathroom with a sink and mirror.

3. PRESIDENTIAL DUPLEX SUITE WITH HOT TUB AND WRANP AROUND BALCONY

PRESIDENTIAL DUPLEX SUITE WITH HOT TUB AND WRANP AROUND BALCONY
Windham
The price is AED 767
AED 958 total
includes taxes & fees
30 Sep - 1 Oct
PRESIDENTIAL DUPLEX SUITE WITH HOT TUB AND WRANP AROUND BALCONY
A dining area with a wooden table, six chairs, a chandelier, and a wall-mounted shelf.

4. 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 AED 735
AED 1,880 total
includes taxes & fees
29 Sep - 30 Sep
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.

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 AED 735
AED 1,837 total
includes taxes & fees
29 Sep - 30 Sep
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
A modern bedroom with a large bed, a dining table, and a view of a forest through large windows.

6. MIRROR CABIN IN THE FOREST WITH HOT TUB

MIRROR CABIN IN THE FOREST WITH HOT TUB
Windham
7.6 out of 10, Good, (5 reviews)
"This was a unique and fun VRBO experience. The cabin was cozy and comfortable.So delightful to wake up to deer walking right by the window! Absolutely a gem of a property!"
United States
Erin J.
The price is AED 768
AED 958 total
includes taxes & fees
1 Oct - 2 Oct
MIRROR CABIN IN THE FOREST WITH HOT TUB
A two-story cabin with a balcony and a chimney, surrounded by a snowy forest.

7. 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 AED 735
AED 1,856 total
includes taxes & fees
29 Sep - 30 Sep
Pines Vignette • Modern 3BR Home in Windham
A large, two-story house with a stone facade, a wooden deck, and a clear sky.

8. 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.
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.

9. 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 AED 1,653
AED 2,293 total
includes taxes & fees
29 Sep - 30 Sep
Charming 2-bedroom townhome in lovely Windham Mountain Village. Walk to skiing.
A cozy living room with wooden walls, a stone fireplace, and a television.

10. Beautiful Windham Chalet 2 minutes to Town and the Mountain

Beautiful Windham Chalet 2 minutes to Town and the Mountain
Windham
10.0 out of 10, Exceptional, (3 reviews)
"Very easy to check in and check out. Very excellent instructions and welcoming atmosphere. "
United States
John K.
The price is AED 1,438
AED 2,287 total
includes taxes & fees
29 Sep - 30 Sep
Beautiful Windham Chalet 2 minutes to Town and the Mountain
A fire pit with two chairs in a backyard.

11. 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 AED 1,282
AED 2,145 total
includes taxes & fees
29 Sep - 30 Sep
NEW OUTDOOR HOT TUB!! 5 BEDROOM/3 BATH CHALET - HAUS WINDHAM
A hot tub with a fire pit, surrounded by Adirondack chairs, and string lights.

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

Luxury Windham Escape w/ Hot Tub, Views & Walk to Mountain
Windham
The price is AED 1,782
AED 3,670 total
includes taxes & fees
30 Sep - 1 Oct
Luxury Windham Escape w/ Hot Tub, Views & Walk to Mountain
A cozy living room with a stone fireplace, a large sectional sofa, a round coffee table, and a wooden ceiling with a loft area.

13. Condo in Windham Mountain Village

Condo in Windham Mountain Village
Windham
10.0 out of 10, Exceptional, (16 reviews)
"Location is great"
United States
Jennifer M.
The price is AED 1,745
AED 2,745 total
includes taxes & fees
29 Sep - 30 Sep
Condo in Windham Mountain Village
A wooden dining area with a fireplace, large windows, and a chandelier.

14. Ski Chalet with Pool, Hot tub, Sauna, Pizza Oven, 2 Fireplaces & Outdoor Firepit

Ski Chalet with Pool, Hot tub, Sauna, Pizza Oven, 2 Fireplaces & Outdoor Firepit
Windham
10.0 out of 10, Exceptional, (9 reviews)
"Great for two families. The main room is awesome to hang out in. The house is clean, and the owner super helpful."
United States
Michael L.
The price is AED 3,231
AED 6,052 total
includes taxes & fees
29 Sep - 30 Sep
Ski Chalet with Pool, Hot tub, Sauna, Pizza Oven, 2 Fireplaces & Outdoor Firepit
Dining

15. Lux Mansion, Windham: Hot Tub, Sauna

Lux Mansion, Windham: Hot Tub, Sauna
Windham
10.0 out of 10, Exceptional, (4 reviews)
"It was a wonderful house. The first few days were very cold and it was spacious and there was a lot to do within the house and it was very comfortable to stay in! When it warmed up we were literally 5 minutes from the slopes and 3 minutes from the town."
United States
RoseMarie D.
The price is AED 3,196
AED 5,875 total
includes taxes & fees
5 Oct - 6 Oct
Lux Mansion, Windham: Hot Tub, Sauna
A kitchen with green cabinets, a stainless steel stove, and a microwave.

16. NEW OUTDOOR HOT TUB! 1-Bedroom Luxury Suite + Full Kitch - Haus Windham

NEW OUTDOOR HOT TUB! 1-Bedroom Luxury Suite + Full Kitch - Haus Windham
Windham
7.6 out of 10, Good, (5 reviews)
"Excellent accommodations, close to everything you could need. My wife and I had a perfect evening "
United States
Anthony M.
The price is AED 575
AED 737 total
includes taxes & fees
29 Sep - 30 Sep
NEW OUTDOOR HOT TUB! 1-Bedroom Luxury Suite + Full Kitch - Haus Windham
A spacious living room with a stone fireplace, wooden staircase, and modern furniture.

17. LUXURY DUPLEX SUITE WITH JACUZZI

LUXURY DUPLEX SUITE WITH JACUZZI
Windham
The price is AED 690
AED 870 total
includes taxes & fees
29 Sep - 30 Sep
LUXURY DUPLEX SUITE WITH JACUZZI
A bedroom with a large bed, a bedside table, a TV mounted on the wall, and a window with curtains.

18. NEW OUTDOOR HOT TUB! 1-Bedroom Luxury Suite + Full Kitchen - Haus Windham

NEW OUTDOOR HOT TUB! 1-Bedroom Luxury Suite + Full Kitchen - Haus Windham
Windham
8.0 out of 10, Very good, (2 reviews)
"This apartment is comfortable, clean and very good location. The hot tub is a plus with the beautiful view. "
United States
Evelyn
The price is AED 602
AED 768 total
includes taxes & fees
7 Oct - 8 Oct
NEW OUTDOOR HOT TUB! 1-Bedroom Luxury Suite + Full Kitchen - Haus Windham
A cozy living room with a leather sofa, a chair, a fireplace, and a stone wall.

19. LUXURY DUPLEX SUITE WITH JACUZZI

LUXURY DUPLEX SUITE WITH JACUZZI
Windham
The price is AED 690
AED 870 total
includes taxes & fees
29 Sep - 30 Sep
LUXURY DUPLEX SUITE WITH JACUZZI
A spacious log cabin interior with a high ceiling, wooden floors, a billiards table, and a cozy seating area.

20. Spacious Cabin near Hunter & Windham Mountains - 5-25-minute drive - 6 Bedrooms

Spacious Cabin near Hunter & Windham Mountains - 5-25-minute drive - 6 Bedrooms
Windham
10.0 out of 10, Exceptional, (2 reviews)
"Great spacious property, inside and out. Great host, Communicative and organized. Special place."
United States
Bryan F.
The price is AED 8,264
AED 11,789 total
includes taxes & fees
5 Oct - 6 Oct
Spacious Cabin near Hunter & Windham Mountains - 5-25-minute drive - 6 Bedrooms
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

8/10 Good
"Great location, friendly staff. Very large rooms but felt a bit musty being that we were on the lower level. The hallway was extremely dark at night, almost hard to see."
Stacy 1-night trip
Posted 17 hours ago
Hunter Lodge, a Bluebird by Lark

Frequently asked questions

Can I find vacation rentals in Windham?

Yes, we give you a choice of vacation rentals close to top points of interest in Windham, or you can select a more remote option if you'd like a relaxing place to stay. Discover why Windham is known for its ski slopes and mountain landscape. While you're here, grab a bite or have a drink at the coffeehouses.

What are some of the best vacation rentals in Windham?

Modern Luxurious Cabin, Catskills - The Tiny Nook: This vacation home rental outside of Windham is located in a rural location and offers a patio, air-conditioning, and WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

How many vacation rentals are there in Windham?

With 139 Expedia vacation rentals, you're sure to find just the right place for your Windham stay.

What can I see and do in Windham?

Elm Ridge Wild Forest and Ashland Park are a couple of lovely local spots to get outside and enjoy nature. Windham Country Club and Windham Mountain Resort are other places to visit while you're in town.

What are vacation rentals like in Windham?

Vacation rentals are privately owned properties you can stay in for a short or long stay in Windham. Vacation rentals offer extras such as kitchens and laundry facilities so your stay will be comfortable. If you're concerned about a clean environment, a vacation rental can provide a sense of seclusion away from shared hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a great option for a small group gathering.