Windham Holiday Rentals

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Check prices for these dates

In two weeks
6 Mar - 8 Mar
In two months
17 Apr - 19 Apr
In three months
15 May - 17 May
In four months
12 Jun - 14 Jun

Our top choices for Windham holiday rentals

Interior

Cozy 1-bedroom studio in peaceful Ashland with AC

Cozy 1-bedroom studio in peaceful Ashland with AC
Ashland
Cozy 1-bedroom studio in peaceful Ashland with AC
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 HK$5,197
HK$8,095 total
includes taxes & fees
23 Feb - 24 Feb
Condo in Windham Mountain Village
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 HK$2,337
HK$2,940 total
includes taxes & fees
2 Mar - 3 Mar
MIRROR CABIN IN THE FOREST WITH HOT TUB
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 HK$1,055
HK$1,739 total
includes taxes & fees
1 Mar - 2 Mar
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, (41 reviews)
"Great place for an incredible price. We would definitely stay here again."
United States
Jason
The price is HK$739
HK$1,220 total
includes taxes & fees
18 Feb - 19 Feb
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
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 HK$5,588
HK$9,354 total
includes taxes & fees
2 Mar - 3 Mar
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 HK$5,588
HK$9,354 total
includes taxes & fees
2 Mar - 3 Mar
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 HK$1,633
HK$2,060 total
includes taxes & fees
11 Mar - 12 Mar
LUXURY DUPLEX SUITE WITH JACUZZI
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 traveller
The price is HK$5,588
HK$9,354 total
includes taxes & fees
2 Mar - 3 Mar
Newly Constructed Modern Farmhouse -- 4 BR / 4.5 Baths, High-end Furnishings!
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, (4 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 HK$5,862
HK$11,842 total
includes taxes & fees
17 Mar - 18 Mar
Lux Chalet-Ski View. 2 Fireplaces. Pool. Hot Tub. Sauna. Pizza Oven
1 bedroom, free WiFi

LUXURY SUITE WITH 2 FULL BEDS

LUXURY SUITE WITH 2 FULL BEDS
Windham
The price is HK$1,141
HK$1,472 total
includes taxes & fees
16 Mar - 17 Mar
LUXURY SUITE WITH 2 FULL BEDS
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 HK$17,585
HK$26,394 total
includes taxes & fees
23 Feb - 24 Feb
Spacious Cabin near Hunter & Windham Mountains - 5-25-minute drive - 6 Bedrooms
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 HK$2,110
HK$4,761 total
includes taxes & fees
2 Mar - 3 Mar
Stylish 3BR Getaway – 3 Minutes to Windham Mountain Resort, AC & WiFi Included!
Iron/ironing board, WiFi, bed sheets

Pines Vignette • Modern 3BR Home in Windham

Pines Vignette • Modern 3BR Home in Windham
Windham
The price is HK$1,057
HK$3,581 total
includes taxes & fees
16 Mar - 17 Mar
Pines Vignette • Modern 3BR Home in Windham
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
9.4 out of 10, Exceptional, (3 reviews)
"We loved ,.. place was very clean and organized "
United States
Cristina L.
The price is HK$1,954
HK$4,566 total
includes taxes & fees
17 Mar - 18 Mar
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
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 HK$1,563
HK$4,178 total
includes taxes & fees
17 Mar - 18 Mar
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 HK$1,026
HK$1,994 total
includes taxes & fees
22 Feb - 23 Feb
Tiny House on Walnut Grove
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 HK$2,043
HK$2,512 total
includes taxes & fees
17 Mar - 18 Mar
GLASS MIRROR CABIN - HAUS WINDHAM
TV

NEW OUTDOOR HOT TUB! Luxury 2 Bedroom Suite -The Haüs Windham

NEW OUTDOOR HOT TUB! Luxury 2 Bedroom Suite -The Haüs Windham
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 HK$1,962
HK$2,410 total
includes taxes & fees
11 Mar - 12 Mar
NEW OUTDOOR HOT TUB! Luxury 2 Bedroom Suite -The Haüs 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 HK$1,469
HK$1,847 total
includes taxes & fees
17 Mar - 18 Mar
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
"So cozy and cute "
Fernanda 1-night trip
Posted 18 hours 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 holiday rentals in Windham?

Yes, there are holiday rentals close to the most popular sights in Windham, or you can select a more secluded option if you're looking for a relaxing 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 coffee shops.

What are some of the best holiday rentals that Windham has to offer?

NEW LISTING! Heated Pool + Sauna + Hot Tub + Game Room + Jungle Gym + Fire Pit: This highly rated holiday home rental in Windham offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a stovetop and a microwave, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with an arcade/games room and 1 hot tub. 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 holiday rentals are there in Windham?

With 152 Expedia holiday rentals, you're guaranteed to find just the right place for your Windham stay.

What can I see and do in Windham?

Ashland Park and Elm Ridge Wild Forest 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 holiday rentals like in Windham?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windham. Holiday rentals offer extras such as laundry facilities and kitchens so you'll have everything you want. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from shared hotel lifts and busy lobbies while still allowing you to travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a popular choice for family gatherings.