
Holiday houses in Windham
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Top-rated holiday rentals in Windham
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VT Cabin sitting above the West River and Village
Converted in 1967 this 1 bedroom, 1 bathroom cozy cabin was once a tractor shed for the historical William's Mills along the West River. It now sits on 12 acres on a country dirt road overlooking the river and the Village. Amenities (stores, dining) are a 1-minute drive, and there are walking trails at the end of the road. It's a great Vermont getaway with ski mountains, Stratton, Bromley, and Magic just minutes away! Cross-country skiing, snowshoeing, and the VT Country store nearby!Yes, Wi-fi!

Summit View Cottage:Ski | Hot tub|Fireplace3bd 2ba
Summit view cottage boasts 3 acres in the beautiful green mountains, we are 1,700 feet up in elevation . At this brand newly built PET FRIENDLY cabin you will have 3 bedrooms and 2 full bathrooms, which will sleep 7 comfortably. We have a brand new 6 person HOT TUB! You will find yourself within 15 minutes to the world famous Stratton mtn, 15 minutes from Bromley mtn and a close 4 minutes to the local Magic mtn.Very close proximity to the town of Manchester, which has great shops and restaurants

Cozy and Romantic Granite Lake Cottage Getaway
Welcome to "Corgi Cottage" ~ your private peaceful getaway to pristine Granite Lake. Enjoy sunrise over the lake from the deck and sunset over the backyard barn. In between, spend the day on the lake in your private sandy cove with dock, fishing, hiking or relaxing. Three mile lake road for walking or biking. The area offers many hiking trails and Mt. Monadnock only 30 minutes away. Small convenience store offers basic amenities while Keene’s many shops and restaurants are only 15 minutes away.

Green Mountain Modern House: iconic modern getaway
Our unique, contemporary home is in the heart of the Green Mountain National Forest, all while offering all the perks of modern luxury in a secluded setting. Our amenities include open concept living and dining room, sauna, wood burning fireplace, front deck, backyard with fire pit and Adirondack chairs, and contemporary design and decor throughout. Now with EV charger, mini-split AC and heat, on-demand backup generator and high speed Starlink wifi (200+ mbs)! Pets welcome with a $100 pet fee.

Riverbed Treehouse @hot tub & a new sauna & views!
The beautiful & brand new Riverbed Treehouse with private sauna and a stunning new hot tub! Views all day long and wildly awesome sunsets!! Stratton mountain is right at your toes with a babbling brook turned raging river in the Spring! Beautiful woods & trails to explore. Stunning ridge line off the ski trails of Magic Mnt!! Close to town for quick shopping & coffee shops! Xcountry ski or snowshoe or walk our groomed trails!! FAST WiFi, nature lovers & a birdwatchers paradise!! @bentapplefarm

Yellow Sweetie at the Base of Stratton
Our adorable home, The Yellow Sweetie, is located in a convenient setting at the base of Stratton Mountain, just 1 minute to the Stratton Resort access road and 8 mins to the slopes. Explore Vermont's many historic towns with classic architecture and covered bridges, as well as its breathtaking mountains, rivers and lakes. The Yellow Sweetie offers stylish country living-meets-shabby chic comfort and coziness. Escape to the fresh Vermont mountain air where life feels a little bit simpler!

Magic Creek
Come enjoy our brand new hot tub! Magic Creek is quintessential Vermont- an antique made modern. The cozy living room with fireplace is an ideal spot to gather at the end of your day. The house has 3 bedrooms and a play room that doubles as a guest room. The house is bordered by a creek with peaceful water falls. Centrally located in the heart of ski country, minutes to Magic Mountain, 20 minutes to Bromley, and 30 to Stratton or Mt Snow, and 40 minutes to Okemo. Come and enjoy it all.

The Owl’s Nest in Landgrove
Our recently renovated cabin is the perfect escape during any season! Located within minutes of Bromley, Magic, and Stratton, Wild Wings, and Viking. Also nestled in an amazing network of hiking, biking and ski trails. Guests will never be more than a few minutes away from outdoor adventure. With two bedrooms and one bonus loft, guests can enjoy the comforts of our cozy cabin, including a full kitchen, bathroom, outdoor shower, HOT TUB, fire pit, WiFi and FREE EV CHARGING. @owlsnestvt

Ogden's Mill Farm
Private guest house situated on over 250 acres, with fully equipped gourmet kitchen and great views of quiet fields and valley. Pond with diving board for swimming in the summer. Giant sledding hill is a favorite of children and adults alike. Trails on property for hiking, xc- skiing, and snowshoeing. 15 mins to Woodstock VT. 45 mins to Killington,Pico and Okemo. Great restaurants and shopping nearby. Hanover and Norwich VT 20 mins. Please note not handicapped accesible.

LUXE Forest Retreat
Here you will experience a full sensory immersion in nature while simultaneously enjoying all the comforts of a custom built luxury home. The SY House derives its name from the Japanese expression Shinrin-yoku, which directly translates to "forest bathing... A practice of therapeutic relaxation where one spends time in a forest or natural atmosphere, focusing on sensory engagement to connect with nature." The essence of this house is nature.

Peaceful Beautiful Mountain Home Spectacular Views
15 Spectacular Acres! Plenty of room for the entire family or great for a couples getaway. This home has everything you need. There are brand new mattresses, quilts, linens, towels, cookware, plates and utensils for your comfort. The beautiful mountain views are seen from just about every room. There is a wood burning fireplace, 4 bedrooms and 2 full bathrooms. Both levels have 3 season porches to enjoy the views, coffee, reading or a meal.

Log Cabin: Amazing Views, River Frontage, Hot Tub
A sparkling clean, recently renovated log cabin in the woods with beautiful views of river and mountains. Located by the charming villages of Williamsville and Newfane, 12 miles from Mount Snow, and right on the crystal clear Rock River. It's the perfect place for a romantic getaway, a family vacation and quality times with good friends. Now also with outdoor hot tub with views of mountains, river and the wide, open sky above.
Popular amenities for Windham holiday rentals
Stay near Windham's top sights
Other great holiday rentals in Windham

Unique private retreat near fishing and hiking.

Stratton Ski House

10 Min to Stratton Resort | Private Hot Tub

Goldfinch Cottage: Timber Frame on 5 Private Acres

New Private Vermont Chalet | Scenic Mountain Views

Bromley Village condo with 3 bedrooms & 2.5 baths

Modern Chalet: Magic Mountain

4 bed/2 bath Home Nestled in Woods Near Mt Snow
When is the best time to visit Windham?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $417 AUD | $398 AUD | $365 AUD | $276 AUD | $317 AUD | $283 AUD | $340 AUD | $341 AUD | $286 AUD | $357 AUD | $334 AUD | $460 AUD |
| Avg. temp | -5°C | -4°C | 1°C | 8°C | 14°C | 18°C | 21°C | 20°C | 16°C | 9°C | 4°C | -2°C |
Frequently Asked Questions
Are there family-friendly vacation rentals in Windham?
Windham has more than 40 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in house rentals in Windham?
Experience the best of Windham with our house rentals, starting at about $200 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly vacation rentals in Windham?
Four-legged friends are welcome in Windham. Choose from more than 20 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Windham?
Yes! Work meets play with ease at over 30 vacation rentals in Windham featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Windham have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Windham. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Windham have a kitchen?
Absolutely! We offer over 30 house rentals with a kitchen in Windham. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Windham have wifi?
Absolutely! We offer over 30 house rentals with wifi in Windham. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Windham have free parking?
Absolutely! We offer over 30 house rentals with free parking in Windham. Enjoy a tailored experience with all the comforts you desire.
Quick stats about holiday rentals in Windham

Total holiday rentals
Explore 60 holiday rentals in Windham

Nightly prices starting at
Windham holiday rentals start at $170 AUD per night before taxes and fees

Verified guest reviews
Over 2,200 verified reviews to help you choose

Family-friendly holiday rentals
40 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
60 of Windham holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Windham rentals

4.9 Average rating
Windham stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
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- Okemo Mountain Resort
- Stratton Mountain
- Killington Resort
- Pats Peak Ski Area
- Magic Mountain Ski Resort
- Monadnock State Park
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Mount Snow Ski Resort
- Ragged Mountain Resort
- Fox Run Golf Club
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Crotched Mountain Ski and Ride
- Montshire Museum of Science
- Dartmouth College
- Mount Sunapee Resort
- Emerald Lake State Park
- Mount Greylock
- Southern Vermont Arts Center
- Massachusetts Museum of Contemporary Art
- Mount Monadnock
- Magic Wings Butterfly Conservatory and Gardens
- Camp Plymouth State Park




