Windsor Holiday Rentals

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Check prices for these dates

In two weeks
5 Jun - 7 Jun
In two months
17 Jul - 19 Jul
In three months
14 Aug - 16 Aug
In four months
11 Sept - 13 Sept

Our top choices for Windsor holiday rentals

Exterior

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
9.4 out of 10, Exceptional, (34 reviews)
"Great property for my stay for business in Leeton …would definitely stay here again !"
United States
Diane D.
The price is HK$979
HK$1,535 total
includes taxes & fees
27 May - 28 May
Newly remodeled, cozy cottage only steps away from the Katy Trail in Windsor, MO
TV

White cabin in the woods close to Univ. of Central Missouri and Whiteman AF Base

White cabin in the woods close to Univ. of Central Missouri and Whiteman AF Base
Warrensburg
9.4 out of 10, Exceptional, (13 reviews)
The price is HK$1,089
HK$1,327 total
includes taxes & fees
24 May - 25 May
White cabin in the woods close to Univ. of Central Missouri and Whiteman AF Base
Interior

Blue Cabin in the woods close to Whiteman AF Base and Univ. of Central Missouri

Blue Cabin in the woods close to Whiteman AF Base and Univ. of Central Missouri
Warrensburg
9.4 out of 10, Exceptional, (16 reviews)
"The cabin was beautiful! Nice, quiet and cozy! Will definitely stay there again!"
United States
Cassie
The price is HK$1,089
HK$1,327 total
includes taxes & fees
24 May - 25 May
Blue Cabin in the woods close to Whiteman AF Base and Univ. of Central Missouri
Smart TV, stereo

Newly Renovated Cabin on Truman Lake Warsaw, Clinton, Bucksaw.

Newly Renovated Cabin on Truman Lake Warsaw, Clinton, Bucksaw.
Deepwater
10.0 out of 10, Exceptional, (47 reviews)
"Beautiful had everything we needed and was very peaceful "
United States
Raelynn W.
The price is HK$972
HK$1,756 total
includes taxes & fees
25 May - 26 May
Newly Renovated Cabin on Truman Lake Warsaw, Clinton, Bucksaw.
Children’s area

Cozy Home w/ Doggy Fence

Cozy Home w/ Doggy Fence
Warsaw
8.8 out of 10, Excellent, (65 reviews)
"The accommodations were good. The location was less than desirable. "
United States
Charlie J.
The price is HK$705
HK$1,518 total
includes taxes & fees
25 May - 26 May
Cozy Home w/ Doggy Fence
Smart TV

The Conservatory

The Conservatory
Sedalia Downtown Historic District
10.0 out of 10, Exceptional, (11 reviews)
"We absolutely loved our stay!! The entire building and our place had so much character while still being modern and updated. "
United States
Brooke M.
The price is HK$1,728
HK$2,447 total
includes taxes & fees
24 May - 25 May
The Conservatory
Terrace/patio

Hickory Hollow Resort

Hickory Hollow Resort
2.0 star property
Clinton
8.0 out of 10, Very good, (18 reviews)
"Nice place to stay "
United States
Sam
The price is HK$621
HK$739 total
includes taxes & fees
21 Jun - 22 Jun
Hickory Hollow Resort
Fridge, microwave, oven, stovetop

Home Away From Home

Home Away From Home
Warrensburg
10.0 out of 10, Exceptional, (40 reviews)
"Great place to stay!!!"
United States
Lynn W.
The price is HK$744
HK$1,399 total
includes taxes & fees
31 May - 1 Jun
Home Away From Home
Exterior

Eagle's Nest - Reel and Trigger

Eagle's Nest - Reel and Trigger
Tom Township
9.0 out of 10, Wonderful, (2 reviews)
"Kinda small but served the purpose for us guys"
United States
Gary A.
The price is HK$1,467
HK$1,684 total
includes taxes & fees
23 Jun - 24 Jun
Eagle's Nest - Reel and Trigger
Interior

The Orchard House: Close to the Katy Trail, Truman Lake and Historic Downtown

The Orchard House: Close to the Katy Trail, Truman Lake and Historic Downtown
Clinton
9.8 out of 10, Exceptional, (28 reviews)
"Perfect place to stay during a weekend family visit!"
United States
Terry M.
The price is HK$811
HK$1,336 total
includes taxes & fees
28 May - 29 May
The Orchard House: Close to the Katy Trail, Truman Lake and Historic Downtown
Private kitchen

Delightful Cabin #4 close to Warrensburg, Knob Knoster, and Clinton.

Delightful Cabin #4 close to Warrensburg, Knob Knoster, and Clinton.
Warrensburg
10.0 out of 10, Exceptional, (2 reviews)
"The cabins are brand new, very clean very nice very spacious. I absolutely love to stay and will definitely be back in refer to family and friends."
United States
Melanie
The price is HK$776
HK$990 total
includes taxes & fees
26 May - 27 May
Delightful Cabin #4 close to Warrensburg, Knob Knoster, and Clinton.
Dining

Unit A Country house near Warrensburg

Unit A Country house near Warrensburg
Warrensburg
10.0 out of 10, Exceptional, (4 reviews)
"The cabin was cozy and perfect for what we needed! Mark was helpful and informative, and we can’t wait to stay here again in the future! Being right next door to Dutch Valley was a perfect bonus!"
United States
Casey S.
The price is HK$932
HK$1,159 total
includes taxes & fees
24 May - 25 May
Unit A Country house near Warrensburg
Exterior

The Bungalow at WAFB/Knob Noster pet friendly

The Bungalow at WAFB/Knob Noster pet friendly
Knob Noster
10.0 out of 10, Exceptional, (17 reviews)
"Awesome clean place many amenities Would stay there again. "
United States
Marcia G.
The price is HK$768
HK$1,260 total
includes taxes & fees
25 May - 26 May
The Bungalow at WAFB/Knob Noster pet friendly
Smart TV, fireplace, books

Downtown Retreat with large privacy fenced yard. Pet Friendly!

Downtown Retreat with large privacy fenced yard. Pet Friendly!
Warrensburg
10.0 out of 10, Exceptional, (55 reviews)
"Very nice place to stay! Only stayed for a few hours because we were just passing through, but the beds were very comfortable!"
United States
Zachary B.
The price is HK$744
HK$1,228 total
includes taxes & fees
22 Jun - 23 Jun
Downtown Retreat with large privacy fenced yard. Pet Friendly!
Fridge, microwave, oven, stovetop

The Lodge - Large Rental

The Lodge - Large Rental
Tom Township
10.0 out of 10, Exceptional, (1 review)
"Had 10 people in the house plenty of room will definitely be staying there again"
United States
Skyler M.
The price is HK$2,725
HK$4,091 total
includes taxes & fees
25 May - 26 May
The Lodge - Large Rental
Smart TV, fireplace, books, music library

Blind Boone Bungalow in the 'Burg– Charming and Stylish 2BR Downtown Retreat

Blind Boone Bungalow in the 'Burg– Charming and Stylish 2BR Downtown Retreat
Warrensburg
10.0 out of 10, Exceptional, (6 reviews)
"Easy communication, super convenient to our destination, clean."
United States
Roxanne B.
The price is HK$901
HK$1,485 total
includes taxes & fees
22 Jun - 23 Jun
Blind Boone Bungalow in the 'Burg– Charming and Stylish 2BR Downtown Retreat
Interior

The Plum Suite

The Plum Suite
Sedalia Downtown Historic District
10.0 out of 10, Exceptional, (2 reviews)
"Nice place to stay, great location "
United States
Jaymi S.
The price is HK$987
HK$1,486 total
includes taxes & fees
25 May - 26 May
The Plum Suite
Smart TV, DVD player, books

Fisherman’s Paradise at The Lake. Charming 2 bedroom house by the lake in Warsaw

Fisherman’s Paradise at The Lake. Charming 2 bedroom house by the lake in Warsaw
Warsaw
10.0 out of 10, Exceptional, (2 reviews)
"Very nice little place. Perfect place to stay for a fishing trip on Truman Lake. "
United States
Caleb T.
The price is HK$1,175
HK$2,431 total
includes taxes & fees
28 May - 29 May
Fisherman’s Paradise at The Lake. Charming 2 bedroom house by the lake in Warsaw
Private kitchen

Cute Little Cabin #3

Cute Little Cabin #3
warrensburg
The price is HK$776
HK$990 total
includes taxes & fees
25 May - 26 May
Cute Little Cabin #3
Dining

Hunters Paradise on The Lake. Cozy 2 bedroom house with large back yard

Hunters Paradise on The Lake. Cozy 2 bedroom house with large back yard
Warsaw
10.0 out of 10, Exceptional, (1 review)
"Very peaceful area.. overnight stay.. convenient to everything.. highly recommend "
United States
David J.
The price is HK$1,175
HK$2,431 total
includes taxes & fees
28 May - 29 May
Hunters Paradise on The Lake. Cozy 2 bedroom house with large back yard
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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Top Windsor Hotel Reviews

Best Western State Fair Inn

Best Western State Fair Inn

6/10 Okay
"Breakfast was over at 9:30 instead of 10. The indoor pool was cold as well at the hot tub."
Douglas 1-night trip
Posted 4 hours ago
Best Western State Fair Inn

Find out more about Windsor

Search for holiday rentals in Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in Windsor using one of the methods below:

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  • Enter your travel dates to view the best deals on holiday rentals in Windsor while they last

Look no further and take a look at our great range of rental properties in Windsor!

Frequently asked questions

Are there holiday rentals in Windsor?

Yes, there are holiday rentals close to the most popular sights in Windsor, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Windsor has to offer?

Whole house on a quiet cove, Lake of the Ozarks, Family owned and operated.: This holiday home rental outside of Windsor is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

What can I see and do in Windsor?

Explore the area and family-friendly sights such as Leisure Park, or get out into nature at a spot like Harry S Truman Reservoir. In the wider area, you’ll find Whiteman Air Force Base and Knob Noster State Park.

What are holiday rentals like in Windsor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windsor. Holiday rentals provide amenities such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a clean environment, a holiday rental can provide a sense of security away from public hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great option for a family trip.