Windham Holiday Rentals

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Check prices for these dates

Tonight
17 Nov - 18 Nov
Tomorrow
18 Nov - 19 Nov
This weekend
21 Nov - 23 Nov
Next weekend
28 Nov - 30 Nov

Holiday Rentals in Windham

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)
"Great place for an incredible price. We would definitely stay here again."
United States
Jason
The price is HK$560
HK$1,024 total
includes taxes & fees
19 Nov - 20 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)
"Check in & checkout and communication super easy. Location is excellent. A/C and hot water great. For 4 guys on a 2 day golf trip it worked fine. "
United States
david d.
The price is HK$770
HK$1,427 total
includes taxes & fees
19 Nov - 20 Nov
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
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)
"Great place to stay very accommodating more than expected "
United States
Julia M.
The price is HK$2,449
HK$3,954 total
includes taxes & fees
19 Nov - 20 Nov
Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!
Exterior
Unwind Windham, Chalet

Unwind Windham, Chalet

Windham
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 HK$1,005
HK$4,019 total
includes taxes & fees
20 Nov - 21 Nov
Unwind Windham, Chalet
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)
"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$5,053
HK$10,912 total
includes taxes & fees
19 Nov - 20 Nov
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)
"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$5,053
HK$10,912 total
includes taxes & fees
19 Nov - 20 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$5,053
HK$10,912 total
includes taxes & fees
19 Nov - 20 Nov
Newly Constructed Modern Farmhouse -- 4 BR / 4.5 Baths, High-end Furnishings!
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$1,974
HK$2,550 total
includes taxes & fees
2 Dec - 3 Dec
MIRROR CABIN IN THE FOREST WITH HOT TUB
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$2,602
HK$4,381 total
includes taxes & fees
20 Nov - 21 Nov
The Cozy Cabins at Walnut Grove- Your Perfect Getaway near Hunter/ Windham
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$1,259
HK$3,879 total
includes taxes & fees
1 Dec - 2 Dec
2 Min Walk to Windham Town | Hot Tub | Fire Pit
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)
"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$5,258
HK$11,211 total
includes taxes & fees
1 Dec - 2 Dec
Lux Chalet-Ski View. 2 Fireplaces. Pool. Hot Tub. Sauna. Pizza Oven
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$2,643
HK$3,038 total
includes taxes & fees
8 Dec - 9 Dec
5 Min to Skiing | Hot Tub | Fire Pit | Pool Table
Terrace/patio
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$2,435
HK$5,954 total
includes taxes & fees
19 Nov - 20 Nov
Drift Haus|4.5BR+ Mountain Lodge
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$5,180
HK$10,396 total
includes taxes & fees
1 Dec - 2 Dec
Serene Catskills Escape: Hot Tub, Pond & Game Room
1 bedroom, free WiFi
LUXURY SUITE WITH 2 FULL BEDS

LUXURY SUITE WITH 2 FULL BEDS

Windham
The price is HK$971
HK$1,278 total
includes taxes & fees
19 Nov - 20 Nov
LUXURY SUITE WITH 2 FULL BEDS
1 bedroom, free WiFi
GLASS MIRROR CABIN - HAUS WINDHAM

GLASS MIRROR CABIN - HAUS WINDHAM

Windham
8.0 out of 10, Very good, (1)
The price is HK$1,624
HK$2,107 total
includes taxes & fees
2 Dec - 3 Dec
GLASS MIRROR CABIN - HAUS WINDHAM
Interior
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$1,113
HK$3,603 total
includes taxes & fees
1 Dec - 2 Dec
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
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$17,490
HK$25,680 total
includes taxes & fees
25 Nov - 26 Nov
Spacious Cabin near Hunter & Windham Mountains - 5-25-minute drive - 6 Bedrooms
Exterior
Condo in Windham Mountain Village

Condo in Windham Mountain Village

Windham
10.0 out of 10, Exceptional, (14)
"Condo was clean and comfortable and very convenient to indoor pool and skiing. Thank you for a great vacation!"
United States
Rich R.
The price is HK$3,498
HK$5,935 total
includes taxes & fees
19 Nov - 20 Nov
Condo in Windham Mountain Village
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$1,020
HK$1,983 total
includes taxes & fees
23 Nov - 24 Nov
Tiny House on Walnut Grove
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
"Clean room"
Lawrence F 2-night trip
Posted 3 days 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
  • 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?

Private Pickleball Ct - Indoor Hot Tub - Spa Room - Lift Tkts : This highly rated holiday home rental in Windham is located on a lake, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Windham?

With 149 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.