Windham County Vacation Rentals

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Top Cities in Windham County

Vacation RentalsVacation Rentals

Stratton

Stratton
Mount Snow featuring mountain biking as well as an individual male
Vacation RentalsVacation Rentals

West Dover

West Dover

Top Vacation Rentals in in Windham County

Exterior
Slopeside Ski-On/Off Condo on Stratton. MNT access for hiking, biking, golf.
10.0 out of 10, Exceptional, (33)
"Great property. Spotless. Had everything we needed. Great information about the area. Bedroom configuration was perfect for us. Great ski on ski off location. Easy parking. Very responsive Host. Would definitely stay there again."
Slopeside Ski-On/Off Condo on Stratton. MNT access for hiking, biking, golf.
Property grounds
Beautiful, private log cabin with huge, relaxing screened porch
10.0 out of 10, Exceptional, (24)
"The house was very comfortable for our family. It was well-stocked with plates, pots, and pans. Bed were comfortable."
Beautiful, private log cabin with huge, relaxing screened porch
Oven, stovetop, dishwasher, coffee/tea maker
VT Cabin overlooking the West River and Village
10.0 out of 10, Exceptional, (19)
"The cabin was perfect for a getaway! Felt secluded however walkable to small village, and within 20 minutes to Stratton. Perfectly stocked to stay in for meals!"
The price is CA $224
CA $462 total
includes taxes & fees
May 21 - May 22
VT Cabin overlooking the West River and Village
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Fridge, microwave, stovetop, coffee/tea maker
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
10.0 out of 10, Exceptional, (22)
"This property is fairytale cute, so welcoming and relaxing. We had a beautiful stay in Vermont thanks to this location. And there were surprise puppies on site!!!!! Honestly this was the kind of trip that gives you confidence in vacation rentals. Clean, wonderfully decorated, off the beaten path a truly relaxing stay! Go outside at night!!!! We dont have stars like that in the city."
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
Exterior
Cozy Cottage Along Idyllic Green River
10.0 out of 10, Exceptional, (33)
"Charming house with everything we needed!"
Cozy Cottage Along Idyllic Green River
Interior
Secluded Escape in Rural Vermont! Sauna Pool, Hot Tub,Game House Mountain Views.
10.0 out of 10, Exceptional, (29)
"We had a wonderful stay. The house has everything you need!"
Secluded Escape in Rural Vermont! Sauna Pool, Hot Tub,Game House Mountain Views.
Fridge, microwave, stovetop, coffee/tea maker
Cozy Falls Brook Cabin: Hike & Swim On-Site!
10.0 out of 10, Exceptional, (4)
"What a beautiful clean cabin nestled next to a brook with lots of hiking paths to explore. Centrally located to several ski resorts. Matt was the most excellent host! I look forward to returning during other seasons!"
Cozy Falls Brook Cabin: Hike & Swim On-Site!
Fridge, microwave, oven, stovetop
Mount Snow's Best View - Sleeps 8-10
10.0 out of 10, Exceptional, (39)
"We loved this condo! It was so gorgeous and clean, and has an awesome view of the mountain. There was so much space and all of our needs were met! We would go back again for sure."
The price is CA $257
CA $766 total
includes taxes & fees
Jun 6 - Jun 7
Mount Snow's Best View - Sleeps 8-10
Property grounds
Cozy cottage tucked away in the woods
10.0 out of 10, Exceptional, (34)
"Stayed here to celebrate a birthday, hang out with friends, and go to Stratton. The house was amazing. We really enjoyed the record player and relaxing by the wood stove. The property was kept nicely and the home was very clean. The house had all of the standard things that are typically needed. We look forward to staying there again next year."
Cozy cottage tucked away in the woods
Property grounds
Mountain Views•Summer Sunsets•Private Hiking Tail•Gameroom•Minimalist
10.0 out of 10, Exceptional, (22)
"The cabin has a well equipped kitchen, is lovingly maintained, with a nice fenced in grassy yard and hiking trails that connect straight to the property. It is very roomy and comfortably hosted 7 of us. Great view from the deck. Amazing view of the heavens with no light pollution at night."
Mountain Views•Summer Sunsets•Private Hiking Tail•Gameroom•Minimalist
Exterior
Catey Rose Retreat|Movie Theatre-Hot Tub-Fireplace
10.0 out of 10, Exceptional, (3)
"We stayed here with 2 other families and our nanny for a ski weekend at Stratton. We had 5 young kids with us and the house was perfect. The owners have thought of everything you’ll need for your stay. Will definitely be back next year."
Catey Rose Retreat|Movie Theatre-Hot Tub-Fireplace
Property grounds
Charming & Cozy River Front Cabin- Close to ski mountains. Ski,Fish,Swim & Hike!
10.0 out of 10, Exceptional, (11)
"Beautiful home with everything that we needed. Short drive to Landmark College to see our daughter and close to Brattleboro shopping and restaurants. The river was also wonderful to wake up to. Highly recommend! "
Charming & Cozy River Front Cabin- Close to ski mountains. Ski,Fish,Swim & Hike!
Fridge, microwave, oven, stovetop
Waterfalls-View-Pond. Secluded Log Cabin Abuts Mt Snow. EV Outlet
9.8 out of 10, Exceptional, (67)
"This home was perfect for our family (with dog) holiday vacation. Very close to Mount Snow and town. The house was comfortable, clean and had everything we needed."
Waterfalls-View-Pond. Secluded Log Cabin Abuts Mt Snow. EV Outlet
TV, fireplace, DVD player, books
Almost Heaven! Vermont wonderland w/ 25 Acres to Explore--Stunning Views!
9.8 out of 10, Exceptional, (104)
"Some friends and I had a wonderful stay at this cabin. A beautiful property with great character and everything we needed for a comfortable stay. We especially loved the wood burning stove and abundant firewood! Would definitely stay again"
Almost Heaven! Vermont wonderland w/ 25 Acres to Explore--Stunning Views!
TV, DVD player, books
Storybook Stratton House: 3 Mi to Mount Snow!
9.8 out of 10, Exceptional, (7)
"Overall the house was great. Exactly as advertised"
Storybook Stratton House: 3 Mi to Mount Snow!
Property grounds
360 degrees of nature from within the 1 bedroom Vermont Mirror House.
9.8 out of 10, Exceptional, (8)
"Beautiful property, amazing views, wonderful owners, warm sauna—what else could you want? Highly recommend!"
The price is CA $476
CA $590 total
includes taxes & fees
May 21 - May 22
360 degrees of nature from within the 1 bedroom Vermont Mirror House.
Exterior
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
9.6 out of 10, Exceptional, (140)
"Great little house to enjoy spending time with family and all that VT has to offer. Wonderful host, we will be back."
The price is CA $231
CA $489 total
includes taxes & fees
May 21 - May 22
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Exterior
Family Friendly Hilltop House In Putney Vermont
9.6 out of 10, Exceptional, (50)
"The house was excellent and the view of the pond was amazing! But what we appreciated the most was Michele's help and communication about the snowstorm that was set to hit the area. She had excellent info and advice and was able to move our stay up a day so we could stay ahead of the storm. We had a great trip to Vermont and very much appreciate her help!"
The price is CA $277
CA $470 total
includes taxes & fees
May 21 - May 22
Family Friendly Hilltop House In Putney Vermont
9 bedrooms, desk, iron/ironing board, free WiFi
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
9.4 out of 10, Exceptional, (16)
"Our experience was average overall."
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
Room, Private Bathroom (Queen Guest Room)
The Inn at Kampfires
3.5 star property
9.4 out of 10, Exceptional, (43)
"We very much enjoyed our stay. The people were super friendly and welcoming!"
The Inn at Kampfires
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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.

Everything you need to know about Windham County vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windham County vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windham County vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Windham County vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windham County. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windham County vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windham County vacation rentals we have selected for you start as low as CA $101 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Windham County rentals

At Expedia, we put the best Windham County vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Windham County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windham County vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windham County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Recent reviews in Windham County
Expedia verified reviews

Black Mountain Inn

Black Mountain Inn

5/5 Excellent
Wonderful staff.
"The hotel was clean and the staff was very welcoming. The hotel was a bit dated, but the mattresses were comfortable and I enjoyed my stay there."
A verified traveller stayed at Black Mountain Inn
Posted 2 days ago
Black Mountain Inn