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Featured Holiday Homes in Windsor

Cabin house on a quiet cove, Lake of the Ozarks near Warsaw Spoonbill Paddlefish

Cabin house on a quiet cove, Lake of the Ozarks near Warsaw Spoonbill Paddlefish

Warsaw
With a stay at this vacation home in Warsaw, you'll be on the waterfront, just steps from Lake of the Ozarks.
Cabin house on a quiet cove, Lake of the Ozarks near Warsaw Spoonbill Paddlefish
Cedar Ridge, 3BR 2 Bath Cabin on Truman Lake

Cedar Ridge, 3BR 2 Bath Cabin on Truman Lake

Deepwater
Located in Deepwater, this vacation home is within a 15-minute drive of Truman Lake and Henry County Museum.
Cedar Ridge, 3BR 2 Bath Cabin on Truman Lake
Home Away From Home

Home Away From Home

Warrensburg
The price is AU$271 per night from 16 Apr to 17 Apr
AU$271
includes taxes & fees
16 Apr - 17 Apr
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
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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
Rm 1 - Waterfront Double Queen / 1st floor

Rm 1 - Waterfront Double Queen / 1st floor

Warsaw
The price is AU$233 per night from 1 May to 2 May
AU$233
includes taxes & fees
1 May - 2 May
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
T's Fish Camp--Crappie Are Biting—Sleeps up to Six

T's Fish Camp--Crappie Are Biting—Sleeps up to Six

Warsaw
With a stay at this vacation home in Warsaw, you'll be on a lake, within a 15-minute drive of Lake of the Ozarks and Truman Lake.
T's Fish Camp--Crappie Are Biting—Sleeps up to Six
Beautiful waterfront house in Warsaw with swimming dock and boat slip

Beautiful waterfront house in Warsaw with swimming dock and boat slip

Warsaw
With a stay at this vacation home in Warsaw, you'll be a 1-minute drive from Lake of the Ozarks and 5 minutes from Benton County Museum.
Beautiful waterfront house in Warsaw with swimming dock and boat slip
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
The price is AU$252 per night from 1 May to 2 May
AU$252
includes taxes & fees
1 May - 2 May
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
Pet Friendly Lodging Close to Whiteman AFB and Warrensburg

Pet Friendly Lodging Close to Whiteman AFB and Warrensburg

Warrensburg
Located in Warrensburg, this vacation home is a 1-minute drive from Knob Noster State Park and 6 minutes from Montserrat Vineyards.
Pet Friendly Lodging Close to Whiteman AFB and Warrensburg
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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
AU$112
Highest Price
AU$271
Popular accommodation
Cabin house on a quiet cove, Lake of the Ozarks near Warsaw Spoonbill Paddlefish, Cedar Ridge, 3BR 2 Bath Cabin on Truman Lake, Home Away From Home , Lake house with a view! Overlooks Warsaw and Lake of the Ozarks, Sleeps 4, Rm 1 - Waterfront Double Queen / 1st floor, T's Fish Camp--Crappie Are Biting—Sleeps up to Six, Beautiful waterfront house in Warsaw with swimming dock and boat slip, Newly remodeled, cozy cottage only steps away from the Katy Trail in Windsor, MO, Pet Friendly Lodging Close to Whiteman AFB and Warrensburg

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
The price is AU$112 per night from 1 May to 2 May
AU$112
includes taxes & fees
1 May - 2 May
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
The price is AU$252 per night from 1 May to 2 May
AU$252
includes taxes & fees
1 May - 2 May
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
Parkfield Inn

Parkfield Inn

2.5 out of 5
506 Kansas Ave, Clinton, MO
Fully refundableReserve now, pay when you stay
The price is AU$184 per night from 4 Apr to 5 Apr
AU$184
includes taxes & fees
4 Apr - 5 Apr
With a stay at Parkfield Inn in Clinton, you'll be within a 5-minute drive of Henry County Museum and Golden Valley Memorial Hospital.
Parkfield Inn
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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
The price is AU$137 per night from 16 Apr to 17 Apr
AU$137
includes taxes & fees
16 Apr - 17 Apr
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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^Subject to availability and chosen travel dates.