Book Holiday Homes in Windsor
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Featured Holiday Homes in Windsor

Bicycle Bungalow New House in Tiny Home Village

Relax at Grandma’s house with a screened in porch overlooking a private lake!

Lake house with a view! Overlooks Warsaw and Lake of the Ozarks, Sleeps 4

Haven House New Comfortable and Clean Retreat

Home Away From Home

Downtown Retreat with large privacy fenced yard. Pet Friendly!

Cozy Home w/ Doggy Fence

Comfy Newly Furnished Home

Rm 1 - Waterfront Double Queen / 1st floor
Windsor Holiday Houses
Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Windsor vacation homes are the perfect way for you to wing it.
Holiday houses in Windsor let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Windsor in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Windsor adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Windsor with your name on it.
No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Windsor vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.
Windsor Holiday Homes essential information
Accommodation | 83 Holiday Homes |
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Lowest Price | |
Highest Price | |
Popular accommodation | Bicycle Bungalow New House in Tiny Home Village, Relax at Grandma’s house with a screened in porch overlooking a private lake!, Lake house with a view! Overlooks Warsaw and Lake of the Ozarks, Sleeps 4, Haven House New Comfortable and Clean Retreat, Home Away From Home , Downtown Retreat with large privacy fenced yard. Pet Friendly!, Cozy Home w/ Doggy Fence, Comfy Newly Furnished Home, Rm 1 - Waterfront Double Queen / 1st floor |
More accommodations in Windsor
Top trending hotels in Windsor

Windsor Crossroads Motel

Newly remodeled, cozy cottage only steps away from the Katy Trail in Windsor, MO

Comfort Inn Sedalia Station

Westbridge Inn and Suites
More ways to explore Windsor
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^Subject to availability and chosen travel dates.