Book Holiday Homes in Windsor

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Featured Holiday Homes in Windsor

Bicycle Bungalow New House in Tiny Home Village

Bicycle Bungalow New House in Tiny Home Village

Sedalia
Located in Sedalia, this vacation home is within a 5-minute drive of Missouri State Fairgrounds and Vermont Park.
Bicycle Bungalow New House in Tiny Home Village
Relax at Grandma’s house with a screened in porch overlooking a private lake!

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

Warsaw
With a stay at this vacation home in Warsaw, you'll be on the waterfront, within a 10-minute drive of Lake of the Ozarks and Benton County Museum.
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

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

Warsaw
With a stay at this vacation home in Warsaw, you'll be on a lake, within a 10-minute drive of Lake of the Ozarks and Benton County Museum.
Lake house with a view! Overlooks Warsaw and Lake of the Ozarks, Sleeps 4
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Haven House New Comfortable and Clean Retreat

Haven House New Comfortable and Clean Retreat

Sedalia
Located in Sedalia, this vacation home is within a 5-minute drive of Missouri State Fairgrounds and Vermont Park.
Haven House New Comfortable and Clean Retreat
Home Away From Home

Home Away From Home

Warrensburg
With a stay at this vacation home in Warrensburg, you'll be a 3-minute walk from University of Central Missouri and 6 minutes by foot from Limetree for ...
Home Away From Home
Downtown Retreat with large privacy fenced yard. Pet Friendly!

Downtown Retreat with large privacy fenced yard. Pet Friendly!

Warrensburg
With a stay at this vacation home in Warrensburg, you'll be a 3-minute walk from Old Drum Statue and 9 minutes by foot from University of Central Missouri.
Downtown Retreat with large privacy fenced yard. Pet Friendly!
Cozy Home w/ Doggy Fence

Cozy Home w/ Doggy Fence

Warsaw
With a stay at this vacation home in Warsaw, you'll be on a lake, within a 10-minute drive of Lake of the Ozarks and Benton County Museum.
Cozy Home w/ Doggy Fence
Comfy Newly Furnished Home

Comfy Newly Furnished Home

Warrensburg
With a stay at this vacation home in Warrensburg, you'll be within a 5-minute drive of Old Drum Statue and University of Central Missouri.
Comfy Newly Furnished Home
Rm 1 - Waterfront Double Queen / 1st floor

Rm 1 - Waterfront Double Queen / 1st floor

Warsaw
With a stay at this hotel in Warsaw, you'll be a 1-minute drive from Lake of the Ozarks and 5 minutes from Benton County Museum.
Rm 1 - Waterfront Double Queen / 1st floor
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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.

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
79 Holiday Homes
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

Top trending hotels in Windsor

Windsor Crossroads Motel

Windsor Crossroads Motel

2.5 out of 5
606 North Main Street, Windsor, MO
Fully refundableReserve now, pay when you stay
When you stay at Windsor Crossroads Motel in Windsor, you'll be 12 minutes by foot from Royal Oaks Hospital.
Windsor Crossroads Motel
Newly remodeled, cozy cottage only steps away from the Katy Trail in Windsor, MO

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

Windsor
When you stay at this vacation home in Windsor, you'll be within a 5-minute drive of Royal Oaks Hospital.
Newly remodeled, cozy cottage only steps away from the Katy Trail in Windsor, MO
Comfort Inn Sedalia Station

Comfort Inn Sedalia Station

2.5 out of 5
3600 W Broadway Blvd, Sedalia, MO
Fully refundableReserve now, pay when you stay
A stay at Comfort Inn Sedalia Station places you in the heart of Sedalia, within a 5-minute drive of Missouri State Fairgrounds and State Fair Community ...
Comfort Inn Sedalia Station
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Westbridge Inn and Suites

Westbridge Inn and Suites

2 out of 5
106 S Baird St., Clinton, MO
Fully refundableReserve now, pay when you stay
Located in Clinton, Westbridge Inn and Suites is within a 5-minute drive of Golden Valley Memorial Hospital and Henry County Museum.
Westbridge Inn and Suites
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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.

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