Windham Vacation Rentals

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Check prices for these dates

In two weeks
Jan 30 - Feb 1
In two months
Mar 13 - Mar 15
In three months
Apr 10 - Apr 12
In four months
May 8 - May 10

Our top choices for Windham vacation rentals

Exterior

Apartment in Windham

Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
9.2 out of 10, Wonderful, (41 reviews)
"Great place for an incredible price. We would definitely stay here again."
United States
Jason
The price is ￥12,096
￥21,602 total
includes taxes & fees
Jan 19 - Jan 20
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
Exterior

Vacation Home in Windham

TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
9.0 out of 10, Wonderful, (55 reviews)
"Nice place and great little town "
United States
PAUL V.
The price is ￥20,635
￥35,264 total
includes taxes & fees
Jan 19 - Jan 20
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Terrace/patio

Cottage in Ashland

Tiny House on Walnut Grove
2.0 star property
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 ￥20,749
￥40,340 total
includes taxes & fees
Jan 20 - Jan 21
Tiny House on Walnut Grove
Interior

Cabin in Windham

Spacious Cabin near Hunter & Windham Mountains - 5-25-minute drive - 6 Bedrooms
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 ￥355,770
￥530,923 total
includes taxes & fees
Jan 28 - Jan 29
Spacious Cabin near Hunter & Windham Mountains - 5-25-minute drive - 6 Bedrooms
1 bedroom, free WiFi

Condo in Windham

LUXURY SUITE WITH 2 FULL BEDS
The price is ￥23,078
￥29,953 total
includes taxes & fees
Jan 20 - Jan 21
LUXURY SUITE WITH 2 FULL BEDS
Outdoor spa tub

Condo in Windham

NEW OUTDOOR HOT TUB! 1-Bedroom Luxury Suite + Full Kitch - Haus 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 ￥39,680
￥50,116 total
includes taxes & fees
Feb 18 - Feb 19
NEW OUTDOOR HOT TUB! 1-Bedroom Luxury Suite + Full Kitch - Haus Windham
Room

Cabin in Windham

MIRROR CABIN IN THE FOREST WITH HOT TUB
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 ￥40,953
￥53,108 total
includes taxes & fees
Jan 21 - Jan 22
MIRROR CABIN IN THE FOREST WITH HOT TUB
Dining

Vacation Home in Windham

2 Min Walk to Windham Town | Hot Tub | Fire Pit
10.0 out of 10, Exceptional, (1 review)
"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 ￥32,415
￥87,776 total
includes taxes & fees
Jan 21 - Jan 22
2 Min Walk to Windham Town | Hot Tub | Fire Pit
Dining

Chalet in Windham

Lux Chalet-Ski View. 2 Fireplaces. Pool. Hot Tub. Sauna. Pizza Oven
10.0 out of 10, Exceptional, (3 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 ￥118,590
￥240,444 total
includes taxes & fees
Feb 3 - Feb 4
Lux Chalet-Ski View. 2 Fireplaces. Pool. Hot Tub. Sauna. Pizza Oven
TV, fireplace

Vacation Home in Windham

Newly Constructed Modern Farmhouse -- 4 BR / 4.5 Baths, High-end Furnishings!
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 ￥120,962
￥199,067 total
includes taxes & fees
Jan 20 - Jan 21
Newly Constructed Modern Farmhouse -- 4 BR / 4.5 Baths, High-end Furnishings!
TV, fireplace

Vacation Home in Windham

Newly Constructed Modern Farmhouse -- 4 BR / 4.5 Baths, High-end Furnishings!
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 ￥120,962
￥199,067 total
includes taxes & fees
Jan 20 - Jan 21
Newly Constructed Modern Farmhouse -- 4 BR / 4.5 Baths, High-end Furnishings!
Microwave, oven, stovetop, dishwasher

Vacation Home in Windham

Newly Constructed Modern Farmhouse -- 4 BR / 4.5 Baths, High-end Furnishings!
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 ￥120,962
￥199,067 total
includes taxes & fees
Jan 20 - Jan 21
Newly Constructed Modern Farmhouse -- 4 BR / 4.5 Baths, High-end Furnishings!
TV, fireplace

Vacation Home in Windham

Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
8.0 out of 10, Very Good, (1 review)
"We loved ,.. place was very clean and organized "
United States
Cristina L.
The price is ￥34,154
￥88,117 total
includes taxes & fees
Jan 27 - Jan 28
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
Smart TV, fireplace

Condo in Windham

Condo in Windham Mountain Village
10.0 out of 10, Exceptional, (14 reviews)
"Place was amazing "
United States
Erik B.
The price is ￥105,150
￥163,768 total
includes taxes & fees
Jan 20 - Jan 21
Condo in Windham Mountain Village
1 bedroom, free WiFi

Condo in Windham

GLASS MIRROR CABIN - HAUS WINDHAM
8.0 out of 10, Very Good, (1 review)
The price is ￥33,039
￥42,869 total
includes taxes & fees
Jan 21 - Jan 22
GLASS MIRROR CABIN - HAUS WINDHAM
TV

Condo in Windham

LUXURY DUPLEX SUITE WITH JACUZZI
The price is ￥47,151
￥61,213 total
includes taxes & fees
Jan 29 - Jan 30
LUXURY DUPLEX SUITE WITH JACUZZI
TV

Condo in Windham

NEW OUTDOOR HOT TUB! Luxury 2 Bedroom Suite -The Haüs Windham
8.0 out of 10, Very Good, (2 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.
The price is ￥40,510
￥52,601 total
includes taxes & fees
Jan 21 - Jan 22
NEW OUTDOOR HOT TUB! Luxury 2 Bedroom Suite -The Haüs Windham
Outdoor spa tub

Condo in Windham

NEW OUTDOOR HOT TUB! 1-Bedroom Luxury Suite + Full Kitchen - Haus Windham
The price is ￥29,719
￥38,566 total
includes taxes & fees
Feb 3 - Feb 4
NEW OUTDOOR HOT TUB! 1-Bedroom Luxury Suite + Full Kitchen - Haus Windham
TV

Condo in Windham

LUXURY DUPLEX SUITE WITH JACUZZI
The price is ￥33,205
￥43,061 total
includes taxes & fees
Feb 3 - Feb 4
LUXURY DUPLEX SUITE WITH JACUZZI
Dining

Condo in Windham

The Haüs Windham - Luxury 2 Bedroom Suite w Loft
The price is ￥60,433
￥78,437 total
includes taxes & fees
Feb 1 - Feb 2
The Haüs Windham - Luxury 2 Bedroom Suite w Loft
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

Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG

Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG

10/10 Excellent
"Everything was great"
Marlon 1-night trip
Posted 16 hours ago
Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG

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. Some other homes for rent in Windham include A'Neils Windham Ski Lodge & Family Retreat and TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores.

How many vacation rentals are there in Windham?

With 149 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.