Windham Vacation Rentals

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Check prices for these dates

In two weeks
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6

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)
"Lovely hosts "
United States
Tyler G.
The price is ￥18,802
￥32,490 total
includes taxes & fees
May 12 - May 13
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Exterior

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, (44 reviews)
"Perfect stay cozy and convenient "
United States
Ahmad O.
The price is ￥11,281
￥20,644 total
includes taxes & fees
May 12 - May 13
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
1 bedroom, in-room safe, iron/ironing board, travel crib

Cozy Boutique Suite · 2 Full Beds · Spa Bathroom · 3 Min to Windham Mtn

Cozy Boutique Suite · 2 Full Beds · Spa Bathroom · 3 Min to Windham Mtn
Windham
The price is ￥21,716
￥28,195 total
includes taxes & fees
May 12 - May 13
Cozy Boutique Suite · 2 Full Beds · Spa Bathroom · 3 Min to Windham Mtn
Smart TV, fireplace

Duplex King Suite · Marble Jacuzzi · Gas Fireplace · Steam Shower · Sleeps 4

Duplex King Suite · Marble Jacuzzi · Gas Fireplace · Steam Shower · Sleeps 4
Windham
The price is ￥31,093
￥40,260 total
includes taxes & fees
May 12 - May 13
Duplex King Suite · Marble Jacuzzi · Gas Fireplace · Steam Shower · Sleeps 4
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 ￥45,124
￥89,345 total
includes taxes & fees
May 12 - May 13
Cozy Family-Friendly A-Frame - 5 min to Windham Mt with AC
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, (7 reviews)
"We loved ,.. place was very clean and organized "
United States
Cristina L.
The price is ￥28,061
￥79,546 total
includes taxes & fees
May 12 - May 13
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
In-room safe, bed sheets

Iconic Glass Mirror Cabin · Forest View · Private Fire Pit · Catskills Hideaway

Iconic Glass Mirror Cabin · Forest View · Private Fire Pit · Catskills Hideaway
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 ￥44,497
￥55,068 total
includes taxes & fees
May 12 - May 13
Iconic Glass Mirror Cabin · Forest View · Private Fire Pit · Catskills Hideaway
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 ￥44,701
￥78,904 total
includes taxes & fees
May 12 - May 13
The Cozy Cabins at Walnut Grove- Your Perfect Getaway near Hunter/ Windham
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 ￥28,202
￥81,053 total
includes taxes & fees
May 19 - May 20
2 Min Walk to Windham Town | Hot Tub | Fire Pit
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 ￥26,087
￥77,585 total
includes taxes & fees
May 25 - May 26
Pines Vignette • Modern 3BR Home in 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 ￥74,423
￥124,034 total
includes taxes & fees
May 17 - May 18
Condo in Windham Mountain Village
Dining

Lux Mansion, Windham: Hot Tub, Sauna, Cold Plunge

Lux Mansion, Windham: Hot Tub, Sauna, Cold Plunge
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 ￥123,777
￥249,422 total
includes taxes & fees
May 18 - May 19
Lux Mansion, Windham: Hot Tub, Sauna, Cold Plunge
Dining

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, (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 ￥117,510
￥240,623 total
includes taxes & fees
May 12 - May 13
Ski Chalet with Pool, Hot tub, Sauna, Pizza Oven, 2 Fireplaces & Outdoor Firepit
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 ￥24,677
￥44,757 total
includes taxes & fees
May 12 - May 13
Tiny House on Walnut Grove
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 ￥100,275
￥136,786 total
includes taxes & fees
May 25 - May 26
Ask about Spring Specials!
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 ￥100,275
￥134,925 total
includes taxes & fees
May 12 - May 13
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 ￥100,275
￥134,925 total
includes taxes & fees
May 12 - May 13
Ask about Spring Specials!
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 ￥352,530
￥527,949 total
includes taxes & fees
May 18 - May 19
Spacious Cabin near Hunter & Windham Mountains - 5-25-minute drive - 6 Bedrooms
Exclusive House, Mountain View | Interior

Red Feather Lodge

Red Feather Lodge
3.0 star property
Windham
The price is ￥313,203
￥338,259 total
includes taxes & fees
May 12 - May 13
Red Feather Lodge
Fridge, microwave, oven, stovetop

King Suite · Full Kitchen · Fireplace · Private Deck · Sleeps 4

King Suite · Full Kitchen · Fireplace · Private Deck · Sleeps 4
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 ￥27,967
￥36,183 total
includes taxes & fees
May 12 - May 13
King Suite · Full Kitchen · Fireplace · Private Deck · Sleeps 4
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

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

10/10 Excellent
"The place is beautiful, offering plenty of privacy. Very clean & comfortable. Would def book again...."
Murrad 2-night trip
Posted 1 day ago
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

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 152 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.