Windsor County holiday accommodation: flats & apartments & more

Discover a selection of 1,500 holiday home rentals in Windsor County that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Stayz holiday homes have the best amenities for hanging out with the people that matter most, including pool and private pool. Prices start at AU$ 374 per night, and flats & apartments and holiday houses are popular options for a stay in Windsor County. Either way, you'll find holiday accommodation for everyone's needs.

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Find the best place to stay — Windsor County

Search 1,506 holiday rentals

Stayed Apr 2021

Ka-bin Weekend

My family and I had the most amazing weekend at the Ka-bin! We stayed two nights, which is not nearly enough time to get the full Vermont experience!! We are already talking about a return trip! I hadn’t seen my daughter in over a year because of Cov...

Stayed Apr 2021

Last of the Season Ski

We went to VT following quarantine and testing to do a last of the season ski at Okemo. The cottage is about 25 miles away. It is mostly a dirt road short cut, but the road was in great condition despite being in the midst of the mud season. The cott...

Stayed Apr 2021

Perfect for large family

The house is just beautiful. The grounds are clean and well kept! My now husband and I decided covid and wedding planning was getting to be too much. We just wanted to be married with our closest family and friends. We had the ceremony on their beaut...

Stayed Mar 2021

Perfect Setting!

This home is incredibly cozy in winter. Well-appointed and fully stocked. There were espresso beans already in the machine and even the bird feeders were filled! After arriving in the dark (not recommended — they are not kidding about the rough roa...

Stayed Mar 2021

Pretty, Clean and Near Everything

I stayed here with my son for a mini-spring break and to celebrate my son's 10th birthday. The apartment is more spacious than the pictures show, it is clean and tidy with everything that you need. That pull-out bed is truly comfortable. We had a gre...

Stayed Mar 2021

Amazing getaway!

My wife, 16 month old daughter and I stayed at Holly and Scott's house for four nights and it was a fantastic experience. Holly was very responsive and informative prior to our arriving with perfectly detailed instructions for checking in and contact...

Stayed Mar 2021

Beautiful Property

We had a great stay in Ludlow. Property was exceptionally clean and exceeded our expectations. Great location. My only suggestion is for bigger sturdier outdoor garbage cans. They were blown over on our arrival which scattered trash and lids across t...

Stayed Mar 2021

Amazing stay at Grahall!

My family and I enjoyed a wonderful week together catching up. As you know, it's been difficult getting together, even with your loved ones, during the pandemic. The house is really an architectural marvel and a special place to stay; a modern castle...

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How many holiday accommodation are available around Windsor County?

Our 2021 accommodation listings offer a large selection of 1,506 holiday rentals around Windsor County. From 534 flats & apartments to 838 holiday houses, find unique holiday homes for you to enjoy a memorable holiday or a weekend with your family and friends. The best place to stay around Windsor County is on Stayz.