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
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

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, (46 reviews)
"Great, highly recommend"
United States
Rebecca
$110 nightly
The price is $118
Nov 8 - Nov 9
Total with taxes and fees
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
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
$173 nightly
The price is $187
Nov 9 - Nov 10
Total with taxes and fees
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 Suite with Jacuzzi, Full Kitchen and Sauna near Windham Mtn

Presidential Suite with Jacuzzi, Full Kitchen and Sauna near Windham Mtn
Windham
$254 nightly
The price is $290
Nov 9 - Nov 10
Total with taxes and fees
Presidential Suite with Jacuzzi, Full Kitchen and Sauna near Windham Mtn
A cozy living room with a stone fireplace, a large sectional sofa, a round coffee table, and a wooden ceiling with a loft area.

4. 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.
$700 nightly
The price is $756
Nov 7 - Nov 8
Total with taxes and fees
Condo in Windham Mountain Village
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
9.0 out of 10, Wonderful, (9 reviews)
"We loved ,.. place was very clean and organized "
United States
Cristina L.
$452 nightly
The price is $488
Nov 9 - Nov 10
Total with taxes and fees
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.

6. 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.
$472 nightly
The price is $510
Nov 8 - Nov 9
Total with taxes and fees
2 Min Walk to Windham Town | Hot Tub | Fire Pit
A spacious living room with a fireplace, a large sofa, a coffee table, and a TV.

7. 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
$556 nightly
The price is $612
Nov 9 - Nov 10
Total with taxes and fees
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.

8. 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
$902 nightly
The price is $974
Nov 9 - Nov 10
Total with taxes and fees
Luxury Windham Escape w/ Hot Tub, Ski on/off one block from Mountain
A large, two-story house with a stone facade, a wooden deck, and a clear sky.

9. 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.
$672 nightly
The price is $725
Nov 8 - Nov 9
Total with taxes and fees
Large Chalet w/ Hot Tub, Fire Pit & 2 Living Rooms + Mins to Town & WMC
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.
$596 nightly
The price is $644
Nov 10 - Nov 11
Total with taxes and fees
Beautiful Windham Chalet 2 minutes to Town and the Mountain
A living room with a sectional sofa, a wooden coffee table, and a view through large arched windows to an outdoor deck.

11. Luxury Windham Retreat w/ Hot Tub & Fireplace, Mins to Slopes

Luxury Windham Retreat w/ Hot Tub & Fireplace, Mins to Slopes
Windham
$817 nightly
The price is $882
Nov 8 - Nov 9
Total with taxes and fees
Luxury Windham Retreat w/ Hot Tub & Fireplace, Mins to Slopes
A two-story cabin with a balcony and a chimney, surrounded by a snowy forest.

12. 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.
$477 nightly
The price is $515
Nov 8 - Nov 9
Total with taxes and fees
Pines Vignette • Modern 3BR Home in Windham
Dining

13. 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.
$1,824 nightly
The price is $1,970
Nov 8 - Nov 9
Total with taxes and fees
Lux Mansion, Windham: Hot Tub, Sauna
A modern bedroom with a large bed, a dining table, and a view of a forest through large windows.

14. Secluded Glass Cabin for Two with Fire Pit and Sauna near Windham Mountain

Secluded Glass Cabin for Two with Fire Pit and Sauna near Windham Mountain
Windham
7.8 out of 10, Good, (6 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.
$265 nightly
The price is $302
Nov 11 - Nov 12
Total with taxes and fees
Secluded Glass Cabin for Two with Fire Pit and Sauna near Windham Mountain
Entryway area

15. 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.
$447 nightly
The price is $483
Nov 7 - Nov 8
Total with taxes and fees
Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!
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.
$2,985 nightly
The price is $3,224
Nov 17 - Nov 18
Total with taxes and fees
Spacious Cabin near Hunter & Windham Mountains - 5-25-minute drive - 6 Bedrooms
A glass-enclosed shower with a handheld showerhead, a glass door, and a white sink with a mirror.

17. 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.
$380 nightly
The price is $410
Nov 7 - Nov 8
Total with taxes and fees
Tiny House on Walnut Grove
An outdoor patio area with a pergola, seating, and a barbecue grill.

18. 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
$402 nightly
The price is $434
Nov 15 - Nov 16
Total with taxes and fees
The Cozy Cabins at Walnut Grove- Your Perfect Getaway near Hunter/ Windham
A spacious living room with a stone fireplace, wooden staircase, and modern furniture.

19. Duplex Suite with Jacuzzi, Steam Shower and Sauna, 3 Min to Windham Mtn

Duplex Suite with Jacuzzi, Steam Shower and Sauna, 3 Min to Windham Mtn
Windham
$207 nightly
The price is $236
Nov 9 - Nov 10
Total with taxes and fees
Duplex Suite with Jacuzzi, Steam Shower and Sauna, 3 Min to Windham Mtn
A spacious living room with a fireplace, a cozy seating area, and a view of the outdoors.

20. 2BR with 2 Baths, Fireplace, Sauna and Gym, 3 Min to Windham Mountain

2BR with 2 Baths, Fireplace, Sauna and Gym, 3 Min to Windham Mountain
Windham
8.6 out of 10, Excellent, (4 reviews)
"Great place. A lot of additional steps and extra pet fee outside of and in addition to typical VRBO booking was a bit of a hassle."
United States
Dan D.
$213 nightly
The price is $243
Nov 9 - Nov 10
Total with taxes and fees
2BR with 2 Baths, Fireplace, Sauna and Gym, 3 Min to Windham Mountain
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 13 hours ago
Hunter Lodge, a Bluebird by Lark

Find out more about Windham

Everything you need to know about Windham vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windham vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windham vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windham vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windham. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Windham in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $162 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windham rentals

At Expedia, we put the best Windham vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Windham rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windham vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windham. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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.