Windham Vacation Rentals

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Check prices for these dates

In two weeks
Apr 10 - Apr 12
In two months
May 22 - May 24
In three months
Jun 19 - Jun 21
In four months
Jul 17 - Jul 19

Our top choices for Windham vacation rentals

Exterior

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, (59 reviews)
"Everything was perfect! Great location!"
United States
Susan I.
The price is ￥17,214
￥30,641 total
includes taxes & fees
Mar 29 - Mar 30
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
1 bedroom, free WiFi

LUXURY SUITE WITH 2 FULL BEDS

LUXURY SUITE WITH 2 FULL BEDS
Windham
The price is ￥21,994
￥28,556 total
includes taxes & fees
Apr 6 - Apr 7
LUXURY SUITE WITH 2 FULL BEDS
TV

Modern Duplex King Suite with Jacuzzi, Steam Shower, Gym — Windham NY Catskills

Modern Duplex King Suite with Jacuzzi, Steam Shower, Gym — Windham NY Catskills
Windham
The price is ￥31,631
￥40,096 total
includes taxes & fees
Mar 30 - Mar 31
Modern Duplex King Suite with Jacuzzi, Steam Shower, Gym — Windham NY Catskills
Room

Unique Mirror Cabin with Private Hot Tub — 3 Min to Windham Mountain

Unique Mirror Cabin with Private Hot Tub — 3 Min to Windham Mountain
Windham
8.0 out of 10, Very Good, (2 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 ￥45,267
￥57,915 total
includes taxes & fees
Mar 29 - Mar 30
Unique Mirror Cabin with Private Hot Tub — 3 Min to Windham Mountain
TV, fireplace

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, (4 reviews)
"We loved ,.. place was very clean and organized "
United States
Cristina L.
The price is ￥34,277
￥87,235 total
includes taxes & fees
Mar 29 - Mar 30
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
Exterior

Pines Vignette • Modern 3BR Home in Windham

Pines Vignette • Modern 3BR Home in Windham
Windham
10.0 out of 10, Exceptional, (2 reviews)
"Staying at this property was an absolute delight. The space was spotless, beautifully decorated, and felt even better in person than in the photos. Every detail - from the comfortable bedding to the amenities - made my stay feel effortless and relaxing. Check in was smooth. Overall an outstanding experience. Highly recommend this property! "
United States
Dikaury G.
The price is ￥21,677
￥74,021 total
includes taxes & fees
Mar 29 - Mar 30
Pines Vignette • Modern 3BR Home in Windham
Property grounds

Cozy Family-Friendly A-Frame - 5 min to Windham Mt with AC

Cozy Family-Friendly A-Frame - 5 min to Windham Mt with AC
Windham
The price is ￥45,703
￥91,691 total
includes taxes & fees
Apr 8 - Apr 9
Cozy Family-Friendly A-Frame - 5 min to Windham Mt with AC
Smart TV, fireplace

Stylish 3BR Getaway – 3 Minutes to Windham Mountain Resort, AC & WiFi Included!

Stylish 3BR Getaway – 3 Minutes to Windham Mountain Resort, AC & WiFi Included!
Windham
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful location amazing townhouse. I will definitely be coming back."
United States
Marquise D.
The price is ￥37,154
￥89,874 total
includes taxes & fees
Mar 29 - Mar 30
Stylish 3BR Getaway – 3 Minutes to Windham Mountain Resort, AC & WiFi Included!
Dining

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 ￥28,690
￥82,628 total
includes taxes & fees
Apr 8 - Apr 9
2 Min Walk to Windham Town | Hot Tub | Fire Pit
Terrace/patio

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 ￥47,626
￥81,904 total
includes taxes & fees
Mar 30 - Mar 31
The Cozy Cabins at Walnut Grove- Your Perfect Getaway near Hunter/ Windham
Smart TV, fireplace

Condo in Windham Mountain Village

Condo in Windham Mountain Village
Windham
10.0 out of 10, Exceptional, (15 reviews)
"Place was amazing "
United States
Erik B.
The price is ￥75,378
￥125,111 total
includes taxes & fees
Mar 30 - Mar 31
Condo in Windham Mountain Village
Dining

Lux Chalet-Ski View. 2 Fireplaces. Pool. Hot Tub. Sauna. Pizza Oven

Lux Chalet-Ski View. 2 Fireplaces. Pool. Hot Tub. Sauna. Pizza Oven
Windham
10.0 out of 10, Exceptional, (7 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 ￥119,018
￥241,482 total
includes taxes & fees
Mar 29 - Mar 30
Lux Chalet-Ski View. 2 Fireplaces. Pool. Hot Tub. Sauna. Pizza Oven
Dining

Waterfront Mansion on 20 acres Windham Ski Resort

Waterfront Mansion on 20 acres Windham Ski Resort
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 ￥126,952
￥251,251 total
includes taxes & fees
Apr 7 - Apr 8
Waterfront Mansion on 20 acres Windham Ski Resort
Interior

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, (1 review)
"Great spacious property, inside and out. Great host, Communicative and organized. Special place."
United States
Bryan F.
The price is ￥357,053
￥528,895 total
includes taxes & fees
Apr 1 - Apr 2
Spacious Cabin near Hunter & Windham Mountains - 5-25-minute drive - 6 Bedrooms
Terrace/patio

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 ￥24,994
￥45,674 total
includes taxes & fees
Mar 27 - Mar 28
Tiny House on Walnut Grove
Microwave, oven, stovetop, dishwasher

Ask about Spring Specials!

Ask about Spring Specials!
Windham
10.0 out of 10, Exceptional, (2 reviews)
"I really enjoyed my time here. The house was comfortable, modern and well taken care of, and the property it was on was beautiful. Good access to town as well, and the full kitchen was well appointed. I had a really relaxing weekend, I'd book this again."
United States
Robert G.
The price is ￥102,010
￥183,906 total
includes taxes & fees
Apr 1 - Apr 2
Ask about Spring Specials!
TV, fireplace

Ask about Spring Specials!

Ask about Spring Specials!
Windham
10.0 out of 10, Exceptional, (4 reviews)
"We had a great three day getaway in Windham. The house was a great spot for a ski getaway in the mountains. Nice open floor plan and every bedroom had a bathroom which was great"
United States
Jim V.
The price is ￥101,562
￥183,099 total
includes taxes & fees
Apr 1 - Apr 2
Ask about Spring Specials!
TV, fireplace

Ask about Spring Specials!

Ask about Spring Specials!
Windham
10.0 out of 10, Exceptional, (1 review)
"We had an amazing time in this magnificent, beautiful home. Our family books ski trips throughout the northeast twice a year as a group of 10 for the past 10 years. This house has by far ranked #1 as the best house we have stayed in. 10 minutes away from the mountain (Windham). 4 large sized bedrooms each with their own large bathrooms. A beautiful dream kitchen with all the essentials. We did plenty of cooking. We loved the open layout of the home. We will definitely be back for sure. "
United States
Anonymous traveler
The price is ￥102,010
￥186,316 total
includes taxes & fees
Apr 1 - Apr 2
Ask about Spring Specials!
Outdoor spa tub

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
10.0 out of 10, Exceptional, (1 review)
"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 ￥28,451
￥36,121 total
includes taxes & fees
Mar 30 - Mar 31
NEW OUTDOOR HOT TUB! 1-Bedroom Luxury Suite + Full Kitchen - Haus Windham
1 bedroom, free WiFi

Glass Mirror Cabin with Hot Tub, Gym, Fire pit on 22 Acres Near Windham Mountain

Glass Mirror Cabin with Hot Tub, Gym, Fire pit on 22 Acres Near Windham Mountain
Windham
8.0 out of 10, Very Good, (1 review)
The price is ￥39,664
￥51,513 total
includes taxes & fees
Mar 30 - Mar 31
Glass Mirror Cabin with Hot Tub, Gym, Fire pit on 22 Acres Near 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

Woodstock Way Hotel

Woodstock Way Hotel

10/10 Excellent
"Everything was wonderful! We'd definitely be happy to return again!"
KATE 1-night trip
Posted 21 hours ago
Woodstock Way Hotel

Find out more about Windham

Search for holiday rentals in Windham on Expedia! You can easily find your home rentals, villas, holiday apartments in Windham using one of the methods below:

  • View our selection of featured holiday rentals in Windham
  • Use the map to find apartments and other holiday homes in the Windham neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Windham while they last

Look no further and take a look at our great range of rental properties in 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?

Private Pickleball Ct - Indoor Hot Tub - Spa Room - Lift Tkts : Visitors like this Windham vacation home rental. It is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Windham?

With 147 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.