
Vacation rentals in Windham
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Top-rated vacation rentals in Windham
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Popular amenities for Windham vacation rentals
Other great vacation rentals in Windham

Spring Hiking Pet Retreat I Game RM l ChimneyHill
Shannon’s place was perfect for our Christmas visit with our son. Clean, spacious, great location, fully stocked, and made the perfect place to host our son and his Copper Mountain colleagues for Christmas!

Breathtaking Lakeside Retreat!
Second year renting. Great place, definitely would recommend. Hope to return next year. Brooke is a fantastic host. Thank you

The Camp
We enjoyed a short ski trip to Berkshire East. M's place was comfortable, spacious and clean. The kitchen had everything we needed to cook and make coffee. They even had dog bowls and treats for our pup! Snow removal was completed early, allowing us to get out and on the slopes for the day. As M says in the description, you definitely need a vehicle with AWD or 4X4 since you are nestled in the mountains. We enjoyed the bountiful binder with history of the small town and local attractions. I would caution people with young children and older folks about the steep staircase to the 2nd floor where the bedrooms are. The 1 full bath is on the first floor so if you're like me, you need to navigate the stairs in the middle of the night. We didn't mind this since it is part of the charm of a historic building and our family of four including two teens had no problems. We enjoyed our stay and would love to return!

Amazing Views, Skiing Nearby and Amenities Galore!
We absolutely loved our stay at Barbara’s home! It was spacious enough to accommodate 6 adults and 1 child with no issue. The kitchen is well appointed, allowing us to cook meals throughout our stay. We had a small storm roll through, which dropped 5” of snow overnight (great for our next day on the mountain!), and we were thrilled to see that the driveway and walkway had been cleared prior to 7am. The bedrooms were comfortable and the view from the great room is truly stunning. Would love to stay here again! Thank you, Barbara!

Your VT Dream House: Fireplace, Pool, Dogs
Beautiful area great amenity. Wish there was 1/2 bath downstairs. That was the only inconvenience.

Large Mount Snow Ski House with Hot Tub
Big group of friends and I stayed at Michele's place for a ski-weekend at Mount Snow. House was comfortable and fun with lots of games in the basement and space for us to hang out as a group in the main living area. Hot tub was 🧑🍳 perfection. Michele was responsive and helpful via messages.

MtSnow * HotTub * Pool * Air Hockey * PingPong * Darts
Place was great! Less than 10 minutes to Mount Snow. We had fun playing ping-pong, air hokey, pool, and darts! Relaxed by the wood burning stove. Lots of rooms and beds.

Luxury Modern Cabin near Okemo & Killington
Stephanie was an Incredible host! The listing matched her description and the property looked even better upon checking in. Stephanie maintains this property really well and I couldn’t have felt any more at home. The home was clean and had a perfect cozy feeling to it. In addition, this was really close to the mountain, which made the getaway even better. I enjoyed the privacy and waking up to a nice snow dusting before my trip to the mountain. I highly suggested staying at Stephanie’s property if you’re looking for a quick getaway. I certainly will be looking to book again soon. Thank you Stephanie!
Quick stats about vacation rentals in Windham
Total rentals
60 properties
Nightly prices starting at
ﺩ.ﺇ367 before taxes and fees
Total number of reviews
2.3K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Frequently Asked Questions
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.
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.
How much does it cost to stay in house rentals in Windham?
Experience the best of Windham with our house rentals, starting at about $150 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
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.
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.
What are the most popular amenities for House Rentals in Windham?
Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with free parking, over 10 homes with air conditioning, over 30 homes with wifi, over 30 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.
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.
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.
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- Okemo Mountain Resort
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Magic Mountain Ski Resort
- Pats Peak Ski Area
- Ragged Mountain Resort
- Monadnock State Park
- Berkshire East Mountain Resort
- Mount Sugarloaf State Reservation
- Mount Greylock Ski Club
- Mount Snow Ski Resort
- Hooper Golf Course
- Baker Hill Golf Club
- Mount Sunapee Resort
- Northern Cross Vineyard
- Willard Mountain
- Stump Sprouts Ski Touring Center
- Clarksburg State Park
- Dorset Field Club
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Ekwanok Country Club
- Killington Adventure Center
- Brattleboro Ski Hill