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
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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.
$125 nightly
The price is $135
Nov 1 - Nov 2
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
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
$215 nightly
The price is $232
Oct 8 - Oct 9
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 Duplex with Jacuzzi, Steam Shower and Private Terrace

Presidential Duplex with Jacuzzi, Steam Shower and Private Terrace
Windham
$247 nightly
The price is $282
Oct 28 - Oct 29
Total with taxes and fees
Presidential Duplex with Jacuzzi, Steam Shower and Private Terrace
A spacious living area with a wooden dining table, a sofa, a fireplace, and a view of the outdoors.

4. 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.
$461 nightly
The price is $498
Nov 3 - Nov 4
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.

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.
$496 nightly
The price is $536
Nov 3 - Nov 4
Total with taxes and fees
2 Min Walk to Windham Town | Hot Tub | Fire Pit
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.
$608 nightly
The price is $657
Oct 8 - Oct 9
Total with taxes and fees
Charming 2-bedroom townhome in lovely Windham Mountain Village. Walk to skiing.
A fire pit with two chairs in a backyard.

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

Private 5BR Chalet Sleeping 12 with Fire Pit near Windham Mtn
Windham
$563 nightly
The price is $619
Oct 26 - Oct 27
Total with taxes and fees
Private 5BR Chalet Sleeping 12 with Fire Pit near Windham Mtn
A hot tub with a fire pit, surrounded by Adirondack chairs, and string lights.

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

Luxury Windham Escape w/ Hot Tub, Views & Walk to Mountain
Windham
$1,067 nightly
The price is $1,153
Oct 20 - Oct 21
Total with taxes and fees
Luxury Windham Escape w/ Hot Tub, Views & Walk to Mountain
A two-story cabin with a balcony and a chimney, surrounded by a snowy forest.

9. 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.
$478 nightly
The price is $516
Nov 1 - Nov 2
Total with taxes and fees
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.

10. 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.
$225 nightly
The price is $256
Oct 28 - Oct 29
Total with taxes and fees
Secluded Glass Cabin in the Woods, 3 Minutes to Windham Mountain
A cozy living room with wooden walls, a stone fireplace, and a television.

11. 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.
$648 nightly
The price is $700
Oct 13 - Oct 14
Total with taxes and fees
Beautiful Windham Chalet 2 minutes to Town and the 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.

12. 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.
$951 nightly
The price is $1,027
Oct 8 - Oct 9
Total with taxes and fees
Condo in Windham Mountain Village
An outdoor patio area with a pergola, seating, and a barbecue grill.

13. 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.
$400 nightly
The price is $431
Oct 8 - Oct 9
Total with taxes and fees
Tiny House on Walnut Grove
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
$545 nightly
The price is $588
Oct 20 - Oct 21
Total with taxes and fees
The Cozy Cabins at Walnut Grove- Your Perfect Getaway near Hunter/ Windham
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.
$1,639 nightly
The price is $1,770
Oct 19 - Oct 20
Total with taxes and fees
Lux Mansion, Windham: Hot Tub, Sauna
A wooden dining area with a fireplace, large windows, and a chandelier.

16. 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, (10 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.
$1,582 nightly
The price is $1,709
Oct 14 - Oct 15
Total with taxes and fees
Ski Chalet with Pool, Hot tub, Sauna, Pizza Oven, 2 Fireplaces & Outdoor Firepit
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
$200 nightly
The price is $228
Oct 28 - Oct 29
Total with taxes and fees
Duplex Suite with Marble Jacuzzi, Steam Shower and Gas Fireplace
A kitchen with green cabinets, a stainless steel stove, and a microwave.

18. 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.
$166 nightly
The price is $189
Oct 28 - Oct 29
Total with taxes and fees
1BR Suite with Full Kitchen and Fireplace, 3 Min to Windham Mtn
A dining area with a large table and chairs, a skylight, and a view of the outdoors.

19. 2BR Suite Sleeping 8 with Two Full Baths, Kitchen and Private Deck

2BR Suite Sleeping 8 with Two Full Baths, Kitchen and Private Deck
Windham
8.0 out of 10, Very good, (3 reviews)
"There is obviously a lot to of remodeling and upgrades going on. New hot tub was not installed. Bathrooms, beds and kitchen were nice. Floors and windows were very dirty. There were no bath washcloths. Perhaps they are not included. The wood exterior side walk is dangerous and needs replaced."
United States
Jackie S.
$224 nightly
The price is $255
Nov 3 - Nov 4
Total with taxes and fees
2BR Suite Sleeping 8 with Two Full Baths, Kitchen and Private Deck
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

The Haüs Windham

The Haüs Windham

10/10 Excellent
"Clean beautiful staff is fabulous kitchen is very well stocked for cooking. Good luck with your establishment thank you for the wonderful stay"
thespena 1-night trip
Posted 5 hours ago
The Haüs Windham

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 $140 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.