
Vacation rentals in Windham County
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Top-rated vacation rentals in Windham County
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Other great vacation rentals in Windham County
Guest favorite

Townhouse in Winhall
4.96 out of 5 average rating, 25 reviewsNew! Vermont Getaway! Stratton - close to skiing!
KatherynRating, 5 stars2 months ago
Excellent location with great parking in a well maintained condo. We had seven people and everyone felt really comfortable. We were able to cook a meal easily and watch a movie after skiing with the family. The rooms are the perfect size and the views are so peaceful. Only a four min drive to Stratton, so it made our weekend simple.
Top guest favorite

Home in Dover
5 out of 5 average rating, 14 reviewsMount Snow - Casa Azul
ElizabethRating, 5 stars1 month ago
We had an amazing time! The location was close to the mountain, had god recommendations in the guest book, and Olivia was very responsive and knowledgeable!
Top guest favorite

Cabin in Wilmington
5 out of 5 average rating, 74 reviewsStoni Woods: Log Home in Southern VT
KimberlyRating, 5 stars1 month ago
We’ve stayed at Beth’s place a few times and absolutely love it - hence why we keep coming back and will continue to do so! She is very communicative and her place is squeaky clean and cozy. We love the log cabin feel and want to go back in the summer since we always go in the winter. This was the first time we brought our dog and she was in heaven! Thanks again, Beth!
Guest favorite

Condo in Dover
4.95 out of 5 average rating, 56 reviewsSki in Ski out condo w/ great amenities included
TingRating, 5 stars3 weeks ago
Great location, steps from the slope, and walkable to the Sundance lodge and parking lot. The host is easy to communicate with and accommodates my last-minute request.
Guest favorite

Home in Wardsboro
4.94 out of 5 average rating, 36 reviewsCozy mountain getaway between Mt. Snow&Stratton
ConnerRating, 5 stars1 month ago
Even better than the pictures. It was a great place for a ski trip. I enjoyed walking around the house and exploring the property. For the price you can’t beat it. I would definitely recommend staying here if you are looking for a place.
Top guest favorite

Condo in Dover
4.98 out of 5 average rating, 48 reviewsMountain View Ski Escape
CarolynRating, 5 stars1 month ago
What a fantastic family weekend (2 families, 5 kids total ages 10 to 6). Andrew was super responsive to questions we had about the sleep set up (two bunks as well as a large single bed w/ trundle) for the kids. But more importantly, he was proactive! He sent clear notes on check in, how to get a fire going, local amenities, shuttles and more. The Community Center was fabulous; a large indoor, heated pool and hot tub, game room, library, TV room w/ bean bag chairs, common room w/ fire, popcorn, hot cocoa and even a little apres ski party on Saturday from 4-6pm. The condo is super close to Mt Snow, easy to find and park. Andrew even had sleds in the front closet which came in handy when the lifts shut down due to wind (but sledding in the backyard was a breeze). Highly recommend this great tri-story condo!
Guest favorite

Home in Dover
4.89 out of 5 average rating, 71 reviewsLarge Mount Snow Ski House with Hot Tub
AndyRating, 5 stars1 month ago
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.
Guest favorite

Home in Wilmington
4.88 out of 5 average rating, 104 reviewsMtSnow * HotTub * Pool * Air Hockey * PingPong * Darts
KevinRating, 5 stars3 weeks ago
⭐️⭐️⭐️⭐️⭐️ Amazing Stay with Wonderful Hosts! Our stay at Matt and Diane’s place was absolutely fantastic! From the very beginning, they were incredibly kind, welcoming, and helpful, ensuring we had everything we needed for a smooth and enjoyable visit. Their communication was excellent before, during, and even after our stay, making us feel truly taken care of. The property itself was exactly as advertised—spotlessly clean, well-equipped, and stocked with all the amenities we could ask for. It was the perfect place to relax and feel at home. Their attention to detail and hospitality made all the difference. I would highly recommend this property to anyone looking for a comfortable and stress-free stay. Thank you, Matt and Diane, for being such amazing hosts—we can’t wait to come back!
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- Okemo Mountain Resort
- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Magic Mountain Ski Resort
- Berkshire East Mountain Resort
- Monadnock State Park
- Saratoga Race Course
- Bousquet Mountain Ski Area
- Mount Sugarloaf State Reservation
- Mount Snow Ski Resort
- Mount Sunapee Resort
- National Museum of Racing and Hall of Fame
- Peebles Island State Park
- Clarksburg State Park
- Stump Sprouts Ski Touring Center
- Pineridge Cross Country Ski Area
- Hildene, The Lincoln Family Home
- Ekwanok Country Club
- Bromley Mountain Ski Resort
- Mount Greylock Ski Club
- Willard Mountain
- Dorset Field Club
- Hancock Shaker Village
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