
Vacation rentals in Windham County
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Windham County
Guests agree: these stays are highly rated for location, cleanliness, and more.
0 of 0 items showing
1 of 3 pages
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Windham County vacation rentals
Other great vacation rentals in Windham County
Guest favorite

Home in Wilmington
5 out of 5 average rating, 11 reviewsOutdoor Enthusiasts Paradise!
EmilyRating, 5 stars2 months ago
Our family had a beautiful, peaceful ski/snowboard vacation at Samantha’s home. The house was exceptionally clean and Samantha was an attentive host. We’ll hopefully visit again!
Guest favorite

Home in Wilmington
4.98 out of 5 average rating, 40 reviewsAPRIL SOVT Retreat l 12minMTSnow l HotTub & Pets
KaylanRating, 5 stars1 month ago
Stephanie and Jason place was an amazing little getaway! Our group had the best time in their cozy house! They were very responsiveness to any messages/questions sent. I would recommend this place to everyone!
Top guest favorite

Cabin in Wilmington
5 out of 5 average rating, 74 reviewsStoni Woods: Log Home in Southern VT
KimberlyRating, 5 stars3 weeks 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
4.94 out of 5 average rating, 53 reviewsSki in Ski out condo great location
ScottRating, 5 stars2 weeks ago
Great location to the mountain and proximity to ski on/off trail. More importantly, the beds were very comfortable and I greatly appreciated the microfiber bedsheets. Rest is a priority for us on trips, but particularly for a ski vacation. Kitchen is well appointed. Great living room space. Only complaint would be the noise of a bottom unit condo by the door, but I’ve been on enough ski trips to know what I was getting into. Exceptional host in regards to communication.
Guest favorite

Home in Wardsboro
4.94 out of 5 average rating, 36 reviewsCozy mountain getaway between Mt. Snow&Stratton
ConnerRating, 5 stars1 week 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 stars2 weeks 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 stars3 weeks 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
4.87 out of 5 average rating, 103 reviewsClose- > MtSnow * HotTub * Pool * Air Hockey * PingPong * Darts
KevinRating, 5 stars2 days 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!
Destinations to explore
- Townhouse rentals Windham County
- Cabin rentals Windham County
- Rentals with a fireplace Windham County
- Private suite rentals Windham County
- Rentals with beach access Windham County
- Fitness-friendly rentals Windham County
- Kid-friendly rentals Windham County
- Waterfront rentals Windham County
- Rentals with a fire pit Windham County
- Rentals with an EV charger Windham County
- Apartment rentals Windham County
- Guesthouse rentals Windham County
- Tiny house rentals Windham County
- Ski-in/ski-out rentals Windham County
- Beachfront rentals Windham County
- Rentals with outdoor seating Windham County
- Rentals with a patio Windham County
- Rentals with an accessible height toilet Windham County
- Rentals with pools Windham County
- Pet-friendly rentals Windham County
- Farmstay rentals Windham County
- House rentals Windham County
- Family-friendly rentals Windham County
- Rentals with a hot tub Windham County
- Rentals with breakfast Windham County
- Bed and breakfasts Windham County
- Rentals with a sauna Windham County
- Rentals with lake access Windham County
- Rentals with a washer and dryer Windham County
- Rentals with a kayak Windham County
- Condo rentals Windham County
- Chalet rentals Windham County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom