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
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

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 SAR 282
SAR 507 total
includes taxes & fees
1 Nov - 2 Nov
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)
"Very nice hosts! Will come back again. Thanks very much!!"
United States
juneid a.
The price is SAR 526
SAR 876 total
includes taxes & fees
18 Oct - 19 Oct
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.

3. Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome

Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
Windham
9.6 out of 10, Exceptional, (8 reviews)
"We loved ,.. place was very clean and organized "
United States
Cristina L.
The price is SAR 605
SAR 1,813 total
includes taxes & fees
3 Nov - 4 Nov
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
A kitchen with green cabinets, a stainless steel stove, and a microwave.

4. 1BR Suite with Full Kitchen and Fireplace, 3 Min to Windham Mtn

1BR Suite with Full Kitchen and Fireplace, 3 Min to Windham Mtn
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 SAR 627
SAR 807 total
includes taxes & fees
3 Nov - 4 Nov
1BR Suite with Full Kitchen and Fireplace, 3 Min to Windham Mtn
A dining area with a wooden table, six chairs, a chandelier, and a wall-mounted shelf.

5. 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 766
SAR 1,976 total
includes taxes & fees
3 Nov - 4 Nov
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.

6. Pines Vignette • Modern 3BR Home in Windham

Pines Vignette • Modern 3BR Home in Windham
Windham
10.0 out of 10, Exceptional, (2 reviews)
The price is SAR 691
SAR 1,939 total
includes taxes & fees
1 Nov - 2 Nov
Pines Vignette • Modern 3BR Home in Windham
A modern bedroom with a large bed, a dining table, and a view of a forest through large windows.

7. Secluded Glass Cabin in the Woods, 3 Minutes to Windham Mountain

Secluded Glass Cabin in the Woods, 3 Minutes to Windham Mountain
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 SAR 973
SAR 1,256 total
includes taxes & fees
26 Oct - 27 Oct
Secluded Glass Cabin in the Woods, 3 Minutes to Windham Mountain
An outdoor patio area with a pergola, seating, and a barbecue grill.

8. Tiny House on Walnut Grove

Tiny House on Walnut Grove
Ashland
4.0 out of 10, (2 reviews)
"Many problems with this listing, first the fire alarm was low on battery, I had to physically climb to reach the smoke detector to detach and remove the battery, a sharp beeping noise went off every 90 seconds and we wouldn’t have been able to sleep without stopping it. There were no spare batteries to change. There were spiders everywhere. My friend used the shower and saw 11 of them moving around the ceiling. They were in the main bed and on the counter and sink as well. The tenant was nice...
United States
Trevor C.
The price is SAR 761
SAR 1,612 total
includes taxes & fees
14 Oct - 15 Oct
Tiny House on Walnut Grove
A fire pit with two chairs in a backyard.

9. Private 5BR Chalet Sleeping 12 with Fire Pit near Windham Mtn

Private 5BR Chalet Sleeping 12 with Fire Pit near Windham Mtn
Windham
The price is SAR 1,626
SAR 2,746 total
includes taxes & fees
26 Oct - 27 Oct
Private 5BR Chalet Sleeping 12 with Fire Pit near Windham Mtn
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 SAR 1,612
SAR 2,670 total
includes taxes & fees
19 Oct - 20 Oct
Beautiful Windham Chalet 2 minutes to Town and the Mountain
Entryway area

11. 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 SAR 1,315
SAR 2,073 total
includes taxes & fees
27 Oct - 28 Oct
Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!
Dining

12. 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 SAR 2,930
SAR 6,194 total
includes taxes & fees
9 Nov - 10 Nov
Lux Mansion, Windham: Hot Tub, Sauna
A hot tub with a fire pit, surrounded by Adirondack chairs, and string lights.

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

Luxury Windham Escape w/ Hot Tub, Views & Walk to Mountain
Windham
The price is SAR 1,704
SAR 3,840 total
includes taxes & fees
20 Oct - 21 Oct
Luxury Windham Escape w/ Hot Tub, Views & Walk to Mountain
An outdoor patio area with a pergola, seating, and a barbecue grill.

14. The Cozy Cabins at Walnut Grove- Your Perfect Getaway near Hunter/ Windham

The Cozy Cabins at Walnut Grove- Your Perfect Getaway near Hunter/ Windham
Ashland
The price is SAR 1,183
SAR 2,028 total
includes taxes & fees
19 Oct - 20 Oct
The Cozy Cabins at Walnut Grove- Your Perfect Getaway near Hunter/ Windham
A cozy living room with a stone fireplace, a large sectional sofa, a round coffee table, and a wooden ceiling with a loft area.

15. 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 SAR 2,498
SAR 3,687 total
includes taxes & fees
14 Oct - 15 Oct
Condo in Windham Mountain Village
A spacious log cabin interior with a high ceiling, wooden floors, a billiards table, and a cozy seating area.

16. 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 SAR 8,451
SAR 12,742 total
includes taxes & fees
20 Oct - 21 Oct
Spacious Cabin near Hunter & Windham Mountains - 5-25-minute drive - 6 Bedrooms
A spacious living room with a stone fireplace, wooden staircase, and modern furniture.

17. Duplex Suite with Marble Jacuzzi, Steam Shower and Gas Fireplace

Duplex Suite with Marble Jacuzzi, Steam Shower and Gas Fireplace
Windham
The price is SAR 765
SAR 982 total
includes taxes & fees
3 Nov - 4 Nov
Duplex Suite with Marble Jacuzzi, Steam Shower and Gas Fireplace
A cozy living room with a leather sofa, a chair, a fireplace, and a stone wall.

18. Two-Level Suite with En-Suite Jacuzzi and Steam Shower in Windham

Two-Level Suite with En-Suite Jacuzzi and Steam Shower in Windham
Windham
The price is SAR 749
SAR 963 total
includes taxes & fees
3 Nov - 4 Nov
Two-Level Suite with En-Suite Jacuzzi and Steam Shower in Windham
A bedroom with a wooden ceiling, a large window, a bed, and a bathroom with a sink and mirror.

19. Presidential Duplex with Jacuzzi, Steam Shower and Private Terrace

Presidential Duplex with Jacuzzi, Steam Shower and Private Terrace
Windham
The price is SAR 1,061
SAR 1,373 total
includes taxes & fees
26 Oct - 27 Oct
Presidential Duplex with Jacuzzi, Steam Shower and Private Terrace
A bedroom with a large window overlooking a snowy forest.

20. Mirrored Glass Cabin for Two with Heated Floors near Windham Mtn

Mirrored Glass Cabin for Two with Heated Floors near Windham Mtn
Windham
6.0 out of 10, (2 reviews)
"The door was not working when we first arrived. We could not get in and could not contact the host. The photos advertised a private hot tub but there is none next to our building. Our fridge was filled with food leftover from the people before us. Makes me wonder if the place was even cleaned. Horrible experience for a 1,500 weekend. And still no response from the host."
United States
Taylor W.
The price is SAR 706
SAR 906 total
includes taxes & fees
3 Nov - 4 Nov
Mirrored Glass Cabin for Two with Heated Floors near Windham Mtn
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

Wylder Hotel Windham

Wylder Hotel Windham

10/10 Excellent
"Loved our stay, will go anytime for a little weekend getaway from nyc!"
Yassaman Modarres 1-night trip
Posted less than an hour ago
Wylder Hotel Windham

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.