Windham Vacation Rentals

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Check prices for these dates

In two weeks
Feb 27 - Mar 1
In two months
Apr 10 - Apr 12
In three months
May 8 - May 10
In four months
Jun 5 - Jun 7

Our top choices for Windham vacation rentals

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, (41 reviews)
"Great place for an incredible price. We would definitely stay here again."
United States
Jason
The price is ￥13,442
￥23,007 total
includes taxes & fees
Feb 10 - Feb 11
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
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, (56 reviews)
"Nice place and great little town "
United States
PAUL V.
The price is ￥21,225
￥35,997 total
includes taxes & fees
Feb 10 - Feb 11
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Interior

Cozy 1-bedroom studio in peaceful Ashland with AC

Cozy 1-bedroom studio in peaceful Ashland with AC
Ashland
The price is ￥23,269
￥48,223 total
includes taxes & fees
Feb 10 - Feb 11
Cozy 1-bedroom studio in peaceful Ashland with AC
1 bedroom, free WiFi

LUXURY SUITE WITH 2 FULL BEDS

LUXURY SUITE WITH 2 FULL BEDS
Windham
The price is ￥22,946
￥29,782 total
includes taxes & fees
Feb 10 - Feb 11
LUXURY SUITE WITH 2 FULL BEDS
Iron/ironing board, WiFi, bed sheets

Pines Vignette • Modern 3BR Home in Windham

Pines Vignette • Modern 3BR Home in Windham
Windham
The price is ￥21,256
￥72,878 total
includes taxes & fees
Feb 10 - Feb 11
Pines Vignette • Modern 3BR Home in Windham
Outdoor spa tub

NEW OUTDOOR HOT TUB! 1-Bedroom Luxury Suite + Full Kitch - Haus Windham

NEW OUTDOOR HOT TUB! 1-Bedroom Luxury Suite + Full Kitch - Haus Windham
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 ￥39,454
￥48,472 total
includes taxes & fees
Mar 5 - Mar 6
NEW OUTDOOR HOT TUB! 1-Bedroom Luxury Suite + Full Kitch - Haus Windham
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 ￥353,745
￥525,863 total
includes taxes & fees
Feb 17 - Feb 18
Spacious Cabin near Hunter & Windham Mountains - 5-25-minute drive - 6 Bedrooms
Room

MIRROR CABIN IN THE FOREST WITH HOT TUB

MIRROR CABIN IN THE FOREST WITH HOT TUB
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 ￥56,442
￥72,805 total
includes taxes & fees
Mar 8 - Mar 9
MIRROR CABIN IN THE FOREST WITH HOT TUB
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, (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 ￥32,230
￥86,257 total
includes taxes & fees
Mar 3 - Mar 4
2 Min Walk to Windham Town | Hot Tub | Fire Pit
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 ￥20,630
￥40,110 total
includes taxes & fees
Feb 10 - Feb 11
Tiny House on Walnut Grove
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 ￥47,166
￥102,048 total
includes taxes & fees
Mar 8 - Mar 9
Stylish 3BR Getaway – 3 Minutes to Windham Mountain Resort, AC & WiFi Included!
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, (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 ￥117,915
￥239,415 total
includes taxes & fees
Feb 22 - Feb 23
Lux Chalet-Ski View. 2 Fireplaces. Pool. Hot Tub. Sauna. Pizza Oven
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
9.0 out of 10, Wonderful, (2 reviews)
"We loved ,.. place was very clean and organized "
United States
Cristina L.
The price is ￥44,022
￥98,653 total
includes taxes & fees
Mar 11 - Mar 12
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
Smart TV, fireplace

Condo in Windham Mountain Village

Condo in Windham Mountain Village
Windham
10.0 out of 10, Exceptional, (14 reviews)
"Place was amazing "
United States
Erik B.
The price is ￥104,551
￥162,836 total
includes taxes & fees
Feb 10 - Feb 11
Condo in Windham Mountain Village
TV, fireplace

Newly Constructed Modern Farmhouse -- 4 BR / 4.5 Baths, High-end Furnishings!

Newly Constructed Modern Farmhouse -- 4 BR / 4.5 Baths, High-end Furnishings!
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
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!

Newly Constructed Modern Farmhouse -- 4 BR / 4.5 Baths, High-end Furnishings!
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 ￥112,412
￥188,176 total
includes taxes & fees
Mar 2 - Mar 3
Newly Constructed Modern Farmhouse -- 4 BR / 4.5 Baths, High-end Furnishings!
TV, fireplace

Newly Constructed Modern Farmhouse -- 4 BR / 4.5 Baths, High-end Furnishings!

Newly Constructed Modern Farmhouse -- 4 BR / 4.5 Baths, High-end Furnishings!
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 ￥120,273
￥197,933 total
includes taxes & fees
Feb 21 - Feb 22
Newly Constructed Modern Farmhouse -- 4 BR / 4.5 Baths, High-end Furnishings!
TV

LUXURY DUPLEX SUITE WITH JACUZZI

LUXURY DUPLEX SUITE WITH JACUZZI
Windham
The price is ￥32,851
￥41,437 total
includes taxes & fees
Mar 2 - Mar 3
LUXURY DUPLEX SUITE WITH JACUZZI
1 bedroom, free WiFi

GLASS MIRROR CABIN - HAUS WINDHAM

GLASS MIRROR CABIN - HAUS WINDHAM
Windham
8.0 out of 10, Very Good, (1 review)
The price is ￥41,105
￥53,415 total
includes taxes & fees
Feb 10 - Feb 11
GLASS MIRROR CABIN - HAUS WINDHAM
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
The price is ￥34,502
￥44,512 total
includes taxes & fees
Mar 8 - Mar 9
NEW OUTDOOR HOT TUB! 1-Bedroom Luxury Suite + Full Kitchen - 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

Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark

10/10 Excellent
"Great room. Good continental breakfast. "
Clayon 1-night trip
Posted 2 days ago
Hunter Lodge, a Bluebird by Lark

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
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  • 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?

TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores: Visitors like this Windham vacation home rental. It is located in the city center and offers a balcony, air-conditioning, and cable TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Some other homes for rent in Windham include A'Neils Windham Ski Lodge & Family Retreat and Private Pickleball Ct - Indoor Hot Tub - Spa Room - Lift Tkts .

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?

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.