Windham Vacation Rentals

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Check prices for these dates

Tonight
Dec 15 - Dec 16
Tomorrow
Dec 16 - Dec 17
This weekend
Dec 19 - Dec 21
Next weekend
Dec 26 - Dec 28

Our top choices for Windham vacation rentals

Outdoor dining
Charming 2-bedroom townhome in lovely Windham Mountain Village. Walk to skiing.

Vacation Home in Windham

Charming 2-bedroom townhome in lovely Windham Mountain Village. Walk to skiing.
2.5 star property
Charming 2-bedroom townhome in lovely Windham Mountain Village. Walk to skiing.
Exterior
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter

Apartment in Windham

Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
9.2 out of 10, Wonderful, (40)
"Great place for an incredible price. We would definitely stay here again."
United States
Jason
The price is ￥13,322
￥22,801 total
includes taxes & fees
Dec 16 - Dec 17
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
Property grounds
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores

Vacation Home in Windham

TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
9.0 out of 10, Wonderful, (54)
"Nice place and great little town "
United States
PAUL V.
The price is ￥22,437
￥37,357 total
includes taxes & fees
Dec 16 - Dec 17
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Exterior
Unwind Windham, Chalet

Vacation Home in Windham

Unwind Windham, Chalet
10.0 out of 10, Exceptional, (2)
"We stayed only one night and we thought that should stay more nights because of the comfort of the house, the location, the amenities and the Property Host was there for answer any question. Definitely we come back now with the conviction that we have everything we need for an escape from New York city. I recommend this place in a 100% for sure. "
United States
Karla R.
The price is ￥45,479
￥109,411 total
includes taxes & fees
Dec 16 - Dec 17
Unwind Windham, Chalet
Terrace/patio
5 Min to Skiing | Hot Tub | Fire Pit | Pool Table

Cabin in Windham

5 Min to Skiing | Hot Tub | Fire Pit | Pool Table
10.0 out of 10, Exceptional, (5)
"Beautiful property, very accurately represented in listing photos. Very well stocked with every thing you need to host. Lots of fun activities to do in the home. Would definitely recommend"
United States
Andrea S.
The price is ￥63,882
￥73,305 total
includes taxes & fees
Dec 17 - Dec 18
5 Min to Skiing | Hot Tub | Fire Pit | Pool Table
Outdoor spa tub
2 Min Walk to Windham Town | Hot Tub | Fire Pit

Vacation Home in Windham

2 Min Walk to Windham Town | Hot Tub | Fire Pit
10.0 out of 10, Exceptional, (1)
"It was amazing for a big family! Tons of space, and everything was very clean! The hosts were also very pleasant to deal with."
United States
Hadassah S.
The price is ￥28,046
￥81,277 total
includes taxes & fees
Dec 17 - Dec 18
2 Min Walk to Windham Town | Hot Tub | Fire Pit
TV, fireplace
Newly Constructed Modern Farmhouse -- 4 BR / 4.5 Baths, High-end Furnishings!

Vacation Home in Windham

Newly Constructed Modern Farmhouse -- 4 BR / 4.5 Baths, High-end Furnishings!
10.0 out of 10, Exceptional, (4)
"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 ￥120,753
￥243,657 total
includes taxes & fees
Dec 18 - Dec 19
Newly Constructed Modern Farmhouse -- 4 BR / 4.5 Baths, High-end Furnishings!
Interior
Newly Constructed Modern Farmhouse -- 4 BR / 4.5 Baths, High-end Furnishings!

Vacation Home in Windham

Newly Constructed Modern Farmhouse -- 4 BR / 4.5 Baths, High-end Furnishings!
10.0 out of 10, Exceptional, (2)
"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 ￥109,067
￥229,069 total
includes taxes & fees
Dec 16 - Dec 17
Newly Constructed Modern Farmhouse -- 4 BR / 4.5 Baths, High-end Furnishings!
Microwave, oven, stovetop, dishwasher
Newly Constructed Modern Farmhouse -- 4 BR / 4.5 Baths, High-end Furnishings!

Vacation Home in Windham

Newly Constructed Modern Farmhouse -- 4 BR / 4.5 Baths, High-end Furnishings!
10.0 out of 10, Exceptional, (1)
"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 ￥109,067
￥229,069 total
includes taxes & fees
Dec 16 - Dec 17
Newly Constructed Modern Farmhouse -- 4 BR / 4.5 Baths, High-end Furnishings!
Fridge, microwave, oven, stovetop
Lux Chalet-Ski View. 2 Fireplaces. Pool. Hot Tub. Sauna. Pizza Oven

Chalet in Windham

Lux Chalet-Ski View. 2 Fireplaces. Pool. Hot Tub. Sauna. Pizza Oven
10.0 out of 10, Exceptional, (3)
"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 ￥111,015
￥219,851 total
includes taxes & fees
Dec 18 - Dec 19
Lux Chalet-Ski View. 2 Fireplaces. Pool. Hot Tub. Sauna. Pizza Oven
Property grounds
Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!

Vacation Home in Ashland

Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!
9.2 out of 10, Wonderful, (5)
"Great place to stay very accommodating more than expected "
United States
Julia M.
The price is ￥49,080
￥78,416 total
includes taxes & fees
Dec 16 - Dec 17
Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!
Room
MIRROR CABIN IN THE FOREST WITH HOT TUB

Cabin in Windham

MIRROR CABIN IN THE FOREST WITH HOT TUB
8.0 out of 10, Very Good, (2)
"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 ￥50,482
￥64,407 total
includes taxes & fees
Jan 13 - Jan 14, 2026
MIRROR CABIN IN THE FOREST WITH HOT TUB
1 bedroom, free WiFi
LUXURY SUITE WITH 2 FULL BEDS

Condo in Windham

LUXURY SUITE WITH 2 FULL BEDS
The price is ￥21,104
￥27,477 total
includes taxes & fees
Dec 16 - Dec 17
LUXURY SUITE WITH 2 FULL BEDS
Terrace/patio
Drift Haus|4.5BR+ Mountain Lodge

Vacation Home in Windham

Drift Haus|4.5BR+ Mountain Lodge
8.0 out of 10, Very Good, (1)
"The property was beautiful and peaceful. The kitchen was amazing and there were so many common areas that were great to socialize in. We did encounter some garbage left by the previous guests, but Will was responsive when we flagged it. There were a few repairs needed on the sliding doors, but overall it was a luxurious place to stay while we enjoyed the nature. "
United States
Grace H.
The price is ￥69,741
￥147,858 total
includes taxes & fees
Dec 18 - Dec 19
Drift Haus|4.5BR+ Mountain Lodge
Microwave, oven, stovetop, dishwasher
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome

Vacation Home in Windham

Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
The price is ￥33,655
￥84,137 total
includes taxes & fees
Dec 18 - Dec 19
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
Exterior
Condo in Windham Mountain Village

Condo in Windham

Condo in Windham Mountain Village
10.0 out of 10, Exceptional, (14)
"Place was amazing "
United States
Erik B.
The price is ￥81,411
￥132,348 total
includes taxes & fees
Dec 16 - Dec 17
Condo in Windham Mountain Village
1 bedroom, free WiFi
GLASS MIRROR CABIN - HAUS WINDHAM

Condo in Windham

GLASS MIRROR CABIN - HAUS WINDHAM
8.0 out of 10, Very Good, (1)
The price is ￥41,718
￥52,544 total
includes taxes & fees
Jan 13 - Jan 14, 2026
GLASS MIRROR CABIN - HAUS WINDHAM
Terrace/patio
Tiny House on Walnut Grove

Cottage in Ashland

Tiny House on Walnut Grove
2.0 star property
4.0 out of 10, (2)
"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 ￥24,540
￥44,845 total
includes taxes & fees
Dec 16 - Dec 17
Tiny House on Walnut Grove
Fridge, microwave, oven, stovetop
Spacious Cabin near Hunter & Windham Mountains - 5-25-minute drive - 6 Bedrooms

Cabin in Windham

Spacious Cabin near Hunter & Windham Mountains - 5-25-minute drive - 6 Bedrooms
10.0 out of 10, Exceptional, (1)
"Great spacious property, inside and out. Great host, Communicative and organized. Special place."
United States
Bryan F.
The price is ￥350,573
￥521,652 total
includes taxes & fees
Dec 22 - Dec 23
Spacious Cabin near Hunter & Windham Mountains - 5-25-minute drive - 6 Bedrooms
TV
NEW OUTDOOR HOT TUB! 1-Bedroom Luxury Suite + Full Kitch - Haus Windham

Condo in Windham

NEW OUTDOOR HOT TUB! 1-Bedroom Luxury Suite + Full Kitch - Haus Windham
7.6 out of 10, Good, (5)
"Excellent accommodations, close to everything you could need. My wife and I had a perfect evening "
United States
Anthony M.
The price is ￥34,193
￥44,282 total
includes taxes & fees
Jan 13 - Jan 14, 2026
NEW OUTDOOR HOT TUB! 1-Bedroom Luxury Suite + Full Kitch - Haus Windham
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
"Everything has exceeded expectations!!!"
Angela 1-night trip
Posted 2 days 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?

A'Neils Windham Ski Lodge & Family Retreat: 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 10 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games. Our travelers also rate Private Pickleball Ct - Indoor Hot Tub - Spa Room - Lift Tkts as a favorite home for rent in Windham.

How many vacation rentals are there in Windham?

With 151 Expedia vacation rentals, you're sure to find just the right place for your Windham stay.

What can I see and do in Windham?

While exploring the area, visit family-friendly sights like Zoom Flume, or get outside and enjoy nature at Ashland Park. 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.