Windsor County Holiday Rentals

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"This was a really nice spacious property. It was very clean and in a nice location. "

"My sister and I stayed the weekend and loved it. The check in/out process was very easy. The host was extremely responsive. The fireplace was a huge bonus as we watched a movie with our popcorn. There are quite a few restaurants within walking distance. It’s perfect. "

includes taxes & fees

4 Dec - 5 Dec

"The property is exactly like the pictures indicate. The house is in a friendly neighborhood outside of town. The house is very comfortable and spacious. The host responds to your messages in timely manner, and, she is very workable. Would definitely stay there again "

"We loved the cabin and its proximity to the town of Woodstock. Nice to come home at the end of the day. The only issue is the bedrooms are upstairs and the bathroom is downstairs….but we managed. Overall a great stay. "

"This is a beautiful property with beautiful views, lots of indoor and outdoor space for the little ones to play, and for the adults to chill and socialize. Very clean and well kept. We would love to come back and stay here again in the future!"

"Beautiful spot in a natural setting. Property owner was very informative about the areas around us as well as the area we were in. A tour of his rescue animals was very enjoyable and informative. It was the perfect getaway. The apartment supplied everything we needed. I would highly recommend a stay there."

"Very cute cabin in the woods. Less than 2 miles off of route 4, which made it easy to get anywhere in Vermont!"

"Many years ago my husband and I had summer access to an identical condo to this one in Solitude Village on Mt. Okemo, so this past week was a real walk down memory lane! The condo was lovely…very clean and well appointed, with sweeping views of the mountains from the master bedroom and living room. The king mattress was very comfortable, and the numerous linens available were fresh, plentiful and high-end. The grounds of Solitude were exquisitely maintained, and while these units do not have AC,...

"Great place - second time we've stayed here. Plenty of space, well-equipped chef's kitchen - great for cooking and entertaining. If you have kids or family and want to cook for them, this is the place you want. Private and cooled in the Spring/Summer by all the trees - great place to stay while visiting Queeche, Woodstock, and beyond."

"Great weekend! Beautiful location !!"

"Our family absolutely loved the property. The house was so cute and had everything necessary. They really thought of everything! We highly recommend staying here if you are looking for a Vermont getaway. "

includes taxes & fees

3 Dec - 4 Dec

"Everything was clean and comfortable and had a great view from the living room/primary bedroom. Because we were there for a wedding we didn't use the kitchen or really get to enjoy all the amenities but the proximity to Woodstock was an added bonus. The shower head in the shared bathroom could use updating but really that's a small complaint. All in all we had a great stay."

"Everything was perfect and as advertised. Very easy to communicate with owner. No issues and offered a very private relaxing getaway. You’ll love it. Worth every penny. "

"All in all it was a great trip. The place was very cute and as described. The upstairs bedrooms are not for light sleepers as the walls only go so far up so they are not really divided. I had read this in other reveiws but honestly for us it wasn't a problem. We went as a family group and it was kind of nice to be able to lay in bed and talk to the others in the room next to you. When we got there the hot tub was so hot that we were not able to get in. Maybe a problem with the thermostat but...

"Terrific and comfortable place to stay! Amazing firepit!"

"Very comfortable home. Loved the nostalgic feeling "

includes taxes & fees

3 Dec - 4 Dec

"Great property, there was everything that we needed for our weekend getaway."

"Obsessed with this house! It was perfect for 2 couples and our pups for a relaxing fall weekend. Rooms were cozy, updated and super clean. The hot tub, fire pit by the river and big kitchen were highlights. I really appreciated the hospitality of having amenities like spices, coffee filters, shampoo & conditioner, laundry detergent, etc. Would book again!"

"The property is well maintained, clean and has a lot of charm. The backyard offers a stunning view of the mountains, a stream and quaint cottages dotting the landscape. The only surprise was the location on a major roadway. Backing into the driveway can be difficult especially after dark. Otherwise we would highly recommend this home. Andrew the property manager was friendly and helpful. "

"This house is exactly as described. It is in a very attractive location with good views and is very private. The house is much larger inside than it appears from the photos but still very cozy and is well equipped. It was spotlessly clean."

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Find out more about Windsor County

Everything you need to know about Windsor 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 Windsor County holiday rental for you. At Expedia, you can take your pick from private holiday 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 Windsor County holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Windsor County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor 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 Windsor County holiday rentals we have chosen for you start as low as AU$423 per night. Entering your travel dates in the search wizard you might find even better deals.

How to find incredible deals on Windsor County rentals

At Expedia, we put the best Windsor 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 Windsor 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 Windsor 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 Windsor 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.

Windsor County Holiday Home Travel Info

Holiday homes	90
Popular accommodation	Windsor County private holiday homes
Known landmarks	Suicide Six Ski Area, Montshire Museum of Science and Buttermilk Falls
International airport	Rutland, VT (RUT-Rutland Southern Vermont Regional)