Windham Holiday Rentals

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Check prices for these dates

In two weeks
21 Nov - 23 Nov
In two months
2 Jan - 4 Jan
In three months
30 Jan - 1 Feb
In four months
27 Feb - 1 Mar

Holiday Rentals in Windham

Exterior detail
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome

Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome

Windham
The price is HK$1,176
HK$3,706 total
includes taxes & fees
10 Nov - 11 Nov
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
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, (40)
"Wonderful coszy spot perfect location for singles and couples even family "
United States
Ahmad O.
The price is HK$560
HK$1,025 total
includes taxes & fees
10 Nov - 11 Nov
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

TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores

Windham
8.8 out of 10, Excellent, (53)
"Very good location and host."
United States
Alexander
The price is HK$770
HK$1,436 total
includes taxes & fees
12 Nov - 13 Nov
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Exterior
Unwind Windham, Chalet

Unwind Windham, Chalet

Windham
10.0 out of 10, Exceptional, (1)
The price is HK$1,713
HK$4,661 total
includes taxes & fees
24 Nov - 25 Nov
Unwind Windham, Chalet
1 bedroom, free WiFi
LUXURY SUITE WITH 2 FULL BEDS

LUXURY SUITE WITH 2 FULL BEDS

Windham
The price is HK$972
HK$1,278 total
includes taxes & fees
11 Nov - 12 Nov
LUXURY SUITE WITH 2 FULL BEDS
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)
"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$1,781
HK$2,312 total
includes taxes & fees
25 Nov - 26 Nov
MIRROR CABIN IN THE FOREST WITH HOT TUB
Outdoor spa tub
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)
"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$1,244
HK$3,864 total
includes taxes & fees
11 Nov - 12 Nov
2 Min Walk to Windham Town | Hot Tub | Fire Pit
Exterior
Drift Haus|4.5BR+ Mountain Lodge

Drift Haus|4.5BR+ Mountain Lodge

Windham
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 HK$1,857
HK$5,336 total
includes taxes & fees
11 Nov - 12 Nov
Drift Haus|4.5BR+ Mountain Lodge
Terrace/patio
Tiny House on Walnut Grove

Tiny House on Walnut Grove

2.0 star property
Ashland
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 HK$1,021
HK$1,984 total
includes taxes & fees
10 Nov - 11 Nov
Tiny House on Walnut Grove
Exterior
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 HK$2,306
HK$4,019 total
includes taxes & fees
17 Nov - 18 Nov
The Cozy Cabins at Walnut Grove- Your Perfect Getaway near Hunter/ Windham
Interior
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)
"We had an absolutely incredible stay at this beautiful Catskills retreat! We booked with Several friends and celebrated their 50th birthday here and it was a wonderful decision. The home was spotless, stylish, and fully equipped with everything we needed for a relaxing and comfortable visit. From the cozy fireplace and spacious deck to the stunning views of the woods and mountains. Set in beautiful and peaceful surroundings, every detail was thoughtfully curated to create the perfect escape....
United States
Carl L.
The price is HK$5,444
HK$11,392 total
includes taxes & fees
22 Nov - 23 Nov
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, (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 traveller
The price is HK$5,444
HK$11,392 total
includes taxes & fees
22 Nov - 23 Nov
Newly Constructed Modern Farmhouse -- 4 BR / 4.5 Baths, High-end Furnishings!
Property grounds
Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!

Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!

Ashland
9.2 out of 10, Wonderful, (5)
"We really enjoyed staying here just because how relaxing it felt, to be outside enjoying the nice weather and having the horses run by. Just overall very soothing and quiet at night."
United States
Richard S.
The price is HK$1,764
HK$3,056 total
includes taxes & fees
17 Nov - 18 Nov
Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!
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)
"Wonderful property. Beautiful house. Great set up for 2 families - one king bedroom and one bedroom with 2 twins upstairs and one king bedroom and one bedroom with 2 twin beds downstairs. Each room has it's own full bathroom. Everything is brand new. First floor is spacious and great for hanging out with open kitchen/dining room/den. Close to Windham and about 25 minute drive from Hunter Mountain. The property manager was very responsive to our concerns and questions. Would definitely rent...
United States
Lauren G.
The price is HK$5,444
HK$11,392 total
includes taxes & fees
22 Nov - 23 Nov
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

Lux Chalet-Ski View. 2 Fireplaces. Pool. Hot Tub. Sauna. Pizza Oven

Windham
10.0 out of 10, Exceptional, (3)
"Everything was super "
United States
Hazal U.
The price is HK$5,537
HK$11,456 total
includes taxes & fees
10 Nov - 11 Nov
Lux Chalet-Ski View. 2 Fireplaces. Pool. Hot Tub. Sauna. Pizza Oven
Fridge, microwave, oven, stovetop
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)
"Great spacious property, inside and out. Great host, Communicative and organized. Special place."
United States
Bryan F.
The price is HK$17,498
HK$26,205 total
includes taxes & fees
15 Nov - 16 Nov
Spacious Cabin near Hunter & Windham Mountains - 5-25-minute drive - 6 Bedrooms
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, (1)
"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$1,625
HK$2,109 total
includes taxes & fees
24 Nov - 25 Nov
NEW OUTDOOR HOT TUB! Luxury 2 Bedroom Suite -The Haüs Windham
Exterior
Serene Catskills Escape: Hot Tub, Pond & Game Room

Serene Catskills Escape: Hot Tub, Pond & Game Room

Windham
10.0 out of 10, Exceptional, (16)
"The house is better than described. We had our annual extended family get together and more room than we needed. The adults and kids enjoyed the game rooms, hot tub movie room. The home was prepared with everything we needed. Very clean We will return. Beautiful home! "
United States
Suzanne n.
The price is HK$5,182
HK$10,317 total
includes taxes & fees
11 Nov - 12 Nov
Serene Catskills Escape: Hot Tub, Pond & Game Room
Exterior
Condo in Windham Mountain Village

Condo in Windham Mountain Village

Windham
10.0 out of 10, Exceptional, (14)
"We had such a great stay at this home which was walking distance (even with little kids) to the mountain! The house was clean and very comfortable."
United States
Kristine M.
The price is HK$2,800
HK$5,098 total
includes taxes & fees
11 Nov - 12 Nov
Condo in Windham Mountain Village
Terrace/patio
5 Min to Skiing | Hot Tub | Fire Pit | Pool Table

5 Min to Skiing | Hot Tub | Fire Pit | Pool Table

Windham
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 HK$3,017
HK$3,463 total
includes taxes & fees
10 Nov - 11 Nov
5 Min to Skiing | Hot Tub | Fire Pit | Pool Table
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

Hotel Vienna

Hotel Vienna

10/10 Excellent
"Room was nice and clean. The staff was beyond friendly and made me feel comfortable and welcomed. Would definitely stay here again!"
Jessica 2-night trip
Posted 15 hours ago
Hotel Vienna

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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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?

Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat: This holiday home rental outside of Windham is located in the mountains, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in Windham?

With 150 Expedia holiday rentals, you're guaranteed 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 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.