Vacation Homes in Windham County

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Top Cities in Windham County

Compare 401 Vacation Homes in Windham County with updated reviews, rates, and availability.

Ski & Ride VT! Private indoor pool to enjoy after a day on the slopes!

9.6 out of 10, Exceptional, (40)
"The owner had the place ready to go when we arrived. It was a late arrival, but there were outside lights that were warm and inviting. Plenty of space for our party of 12 (6 adults and 6 kids). Kitchen was welled stocked with cooking necessities, great hangout spaces in the basement and first floor, and a convenient space for ski boots and outer gear in the basement near parking. Kids absolutely loved the pool - and have the pruned hands to prove it. The location couldn't have been better, ~25...
Ski & Ride VT! Private indoor pool to enjoy after a day on the slopes!

SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!

9.0 out of 10, Wonderful, (41)
"We had a group of thirty-four people for a family vacation and had a blast. The host and the housekeeper were tremendously responsive to any small issues we had over the first few days. The kitchen was well stocked but could use more mugs for coffee/tea and additional forks for larger groups and the tea bags were past the best before date and should be replaced. Twelve bedrooms, each with their own bathroom was great. The pool, hot tubs, ping pong table, pool table, tennis court, and fire pit...
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!

Modern Ski In / Ski Out 4BR / 3BA Smart Home w/ Private Hot Tub and shared pool

10.0 out of 10, Exceptional, (9)
"We had a wonderful stay. We enjoyed the home and community amenities. Location was great and our family enjoyed the convenience of having the access to ski on / ski off. We look forward to our stay next year!"
Modern Ski In / Ski Out 4BR / 3BA Smart Home w/ Private Hot Tub and shared pool

Walk to Mt. Snow! Hot tub! Sauna! Sleeps 16

10.0 out of 10, Exceptional, (21)
"The property is exactly as described! We loved the proximity to the mountain. The house is adorable and perfectly suited for our family. The host was VERY responsive and had great customer service during our stay. We can not wait to come back again!"
Walk to Mt. Snow! Hot tub! Sauna! Sleeps 16

500ft across the street to Carnitha. Gromet to main lift or take Moover to Base

10.0 out of 10, Exceptional, (32)
"We had the most enjoyable and comfortable stay at this lovely home away from home! Jen was more than welcoming and always very responsive. The house was very clean and located conveniently across the street from the mountains. Looking forward to staying here again next season! :)"
500ft across the street to Carnitha. Gromet to main lift or take Moover to Base

Secluded Vermont Retreat w/ 25 Acres to Explore--Dog Heaven! Mountain Views!

9.8 out of 10, Exceptional, (110)
"Every need accommodated including a back-up generator! Well appointed kitchen and bathrooms. Very cozy and spacious home inside. Very comfortable bed mattress in master bedroom. Lots of yard for dogs to run free. Nature all around. Lots of books and board games there. Laundry room was a big plus. Remote setting but lots to see and explore within reach. Very lovely stay and hosts were very responsive."
Secluded Vermont Retreat w/ 25 Acres to Explore--Dog Heaven! Mountain Views!

Spacious Townhome with breathtaking views of Mount Snow. 5 min Shuttle to ski

10.0 out of 10, Exceptional, (17)
"We had an amazing stay at this spacious townhome, just across from Mount Snow. The location was perfect for hiking, with stunning trails to explore throughout the area. We spent our days hiking and taking in the beautiful mountain views. The townhome is beautifully decorated and very comfortable. The living area with a cozy wood-burning fireplace was perfect for relaxing after a day outdoors. The fully equipped kitchen made it easy to cook and enjoy meals together, and we loved spending time on...
Spacious Townhome with breathtaking views of Mount Snow. 5 min Shuttle to ski

Beautiful 4 Bedroom Townhome Minutes from Mt Snow

9.6 out of 10, Exceptional, (19)
"The property has a great location to so many activities, shops and places to eat. The house was a few steps from the pool which my kids loved"
Beautiful 4 Bedroom Townhome Minutes from Mt Snow

Hilltop Home with Great Views

9.2 out of 10, Wonderful, (12)
"Michelle made our experience super easy and memorable! Drive up a private road and a pretty steep hill (4wd a must in winter) to a secluded, beautiful house with plenty of space. Just you and nature. The house itself has all the amenities - full kitchen, sitting areas, and even a wood stove that Michelle started up before we got there. Beds are comfortable, and the bathrooms have insane mountaintop views. Michele even left a few eggs for starter breakfast which was much appreciated. You can’t...
Hilltop Home with Great Views

'Luna Stella' - West Dover Home 1 Mi. to Mt Snow!

9.8 out of 10, Exceptional, (63)
"Great property. Enjoyed our stay."
'Luna Stella' - West Dover Home 1 Mi. to Mt Snow!

Modern Mount Snow Retreat with Walk to Ski Lifts & Lodge

10.0 out of 10, Exceptional, (11)
"If you are looking for either Fall getaway along VT-100 or snow adventures this place is located with easy access to a variety of wonderful local restaurants, breweries, shopping and outdoor adventures. Bathroom and kitchen stocked with basic necessities. Great communication with hosts. Will definitely be back! "
The price is SAR 1,048
SAR 2,308 total
includes taxes & fees
27 Nov - 28 Nov
Modern Mount Snow Retreat with Walk to Ski Lifts & Lodge

Family Home w/ Great Yard, Fireplace, Kayaks, AC & WiFi - Near Skiing/Lakes

10.0 out of 10, Exceptional, (18)
"Everything about this house was great! We will definitely be back!"
Family Home w/ Great Yard, Fireplace, Kayaks, AC & WiFi - Near Skiing/Lakes

Sunny Stratton Townhome ~ 1 Mi to Skiing!

10.0 out of 10, Exceptional, (4)
"Wonderful and clean townhome! Perfect location to be close to Stratton Resort. Thank you!"
Sunny Stratton Townhome ~ 1 Mi to Skiing!

West Dover Home w/ Deck, Grill & EV Outlet

9.8 out of 10, Exceptional, (16)
"Long weekend ski trip to Mt. Snow with three families. Layout of bedrooms and living spaces was perfect. Location to Mt. Snow and area market and restaurants was also perfect. We’ll be back."
West Dover Home w/ Deck, Grill & EV Outlet

Three Bedroom home with loft

Three Bedroom home with loft

Spacious Family getaway near Magic Mountain, VT

9.4 out of 10, Exceptional, (3)
"Perfect house for family with kids ! Plenty of room for three families !"
Spacious Family getaway near Magic Mountain, VT

Beautiful dog-friendly house w/ fireplace, firepit, bbq, deck, patio, w/d, wifi

Beautiful dog-friendly house w/ fireplace, firepit, bbq, deck, patio, w/d, wifi

Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

The price is SAR 1,378
SAR 2,464 total
includes taxes & fees
1 Dec - 2 Dec
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

Countryside, mountain-view house near eagle's nest with patios - dog-friendly

9.4 out of 10, Exceptional, (3)
"Everything about the listing was accurate. It was very clean and had cute decor that reqlly felt like youre in vermont. The little neighborhood is very cute, quiet and safe feeling. Ita right by my friends house and will most likely be booking again!"
Countryside, mountain-view house near eagle's nest with patios - dog-friendly

1/2 Mi to Ski: Secluded Home in Vermont

1/2 Mi to Ski: Secluded Home in Vermont
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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