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Windham County Accommodation: Most Popular Cities to Stay

Holiday RentalsHoliday Rentals

Stratton

Stratton

Top Holiday Rentals in Windham County

VT Cabin overlooking the West River and Village
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 £275
per night
1 May - 2 May
VT Cabin overlooking the West River and Village
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
Fridge, microwave, oven, stovetop
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
10.0 out of 10, Exceptional, (28)
"This is a great spot for a getaway! The space was spotless. There was a lot of privacy. The location was close to everything we needed. The space is cozy and super fun with the hot tub and fore pit! We we are able to enjoy the included breakfast, which was great before skiing!"
The price is £364
per night
1 May - 2 May
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
Slopeside Ski-On/Off Condo on Stratton. MNT access for hiking, biking, golf.
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.
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Dream Stratton Forest Cabin w/Hot Tub & Fast WiFi
Exterior
Dream Stratton Forest Cabin w/Hot Tub & Fast WiFi
10.0 out of 10, Exceptional, (27)
"This was one of the best locations we have stayed at! We came up for a fundraiser at Stratton Mountain. Tommy was so helpful and provided great information from booking up until checkout. There is a great virtual guide that answers all important questions. The house and outdoors were exactly what we were looking for. Our dog loved running around and we enjoyed the hot tub. The house was very clean and had all the necessities we needed. Our favorite part was being cozy on the coach watching...
Dream Stratton Forest Cabin w/Hot Tub & Fast WiFi
Secluded Escape in Rural Vermont! Sauna Pool, Hot Tub,Game House Mountain Views.
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.
Mount Snow's Best View - Sleeps 8-10
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."
Mount Snow's Best View - Sleeps 8-10
Beautiful, private log cabin with huge, relaxing screened porch
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
Cozy Cottage Along Idyllic Green River
Exterior
Cozy Cottage Along Idyllic Green River
10.0 out of 10, Exceptional, (32)
"Perfect litle getaway. Not to far from town, beautiful surrounding area, exactly what i was looking for."
Cozy Cottage Along Idyllic Green River
Catey Rose Retreat|Movie Theatre-Hot Tub-Fireplace
Outdoor dining
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
Charming & Cozy River Front Cabin- Close to ski mountains. Ski,Fish,Swim & Hike!
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!
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
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!
Cozy Falls Brook Cabin: Hike & Swim On-Site!
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!
Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester
Property grounds
Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester
10.0 out of 10, Exceptional, (12)
"Nice house, clean, easy access, well set up for family skiing."
Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester
Potter's Place | House in Jamaica with mountain views
Fridge, microwave, oven, stovetop
Potter's Place | House in Jamaica with mountain views
10.0 out of 10, Exceptional, (2)
"The house was warm, clean, peaceful and comfortable for our short stay. We were in VT to ski at Stratton but I would love to come back in other seasons to explore the nearby state parks. I would gladly stay at this property again."
Potter's Place | House in Jamaica with mountain views
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
9 bedrooms, desk, iron/ironing board, free WiFi
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
9.8 out of 10, Exceptional, (14)
"Large property with multiple houses. Main house had plenty of room for our group of 14, and the guest house was a bonus area to hang out at night! The host was very responsive and easy to communicate with."
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
Seasons On Mount Snow - Ski-in/Ski-out
Indoor pool, a heated pool
Seasons On Mount Snow - Ski-in/Ski-out
9.8 out of 10, Exceptional, (148)
"Carl was super nice, proactive, and a great communicator for this trip. The place was convenient, clean, in great repair, with lots of amenities and super easy to ski out. Little touches like a box of firewood, tinder, and matches and clear instructions on everything make things so pleasant. Would totally stay again. "
Seasons On Mount Snow - Ski-in/Ski-out
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
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 £292
per night
1 May - 2 May
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
5 minute walk to lifts and Stratton Village! Cozy fireplace with a private patio
Outdoor pool, a heated pool
5 minute walk to lifts and Stratton Village! Cozy fireplace with a private patio
9.6 out of 10, Exceptional, (8)
"Great place. Super close to everything. Host was super helpful. Everything you need for an amazing ski weekend."
5 minute walk to lifts and Stratton Village! Cozy fireplace with a private patio
Jacksonville Cabin w/ Wraparound Deck & Views
Fridge, microwave, stovetop, dishwasher
Jacksonville Cabin w/ Wraparound Deck & Views
9.6 out of 10, Exceptional, (23)
"Magical little place."
Jacksonville Cabin w/ Wraparound Deck & Views
Family Friendly Hilltop House In Putney Vermont
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 £268
per night
7 May - 8 May
Family Friendly Hilltop House In Putney Vermont
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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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windham County holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Windham County holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windham County holiday rentals we have selected for you start as low as £268 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 holiday 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 holiday.

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

Vikings Villages

Vikings Villages

5/5 Excellent
This is what I need
"I would leave all my possessions behind to live in this cabin forever."
A verified traveller stayed at Vikings Villages
Posted 2 days ago
Vikings Villages