Windsor Holiday Rentals

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Holiday Rentals in Windsor

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

9.6 out of 10, Exceptional, (26)
"I wanted an escape to nature. This wasn't it. The newly renovated home/cabin was very clean & convenient inside. Faced directly at another property & backed by a questionable neighborhood. Comfortable, amenities were many. "
The price is AU$243
includes taxes & fees
30 Nov - 1 Dec
Newly remodeled, cozy cottage only steps away from the Katy Trail in Windsor, MO

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

9.4 out of 10, Exceptional, (8)
"The cabin was very clean and bigger than I expected from pictures. Hosts were helpful. "
The price is AU$247
includes taxes & fees
1 Dec - 2 Dec
Blue Cabin in the woods close to Whiteman AF Base and Univ. of Central Missouri

Plenty of charm and room in the center of Warrensburg, Missouri 64093

4.0 out of 10, (1)
Plenty of charm and room in the center of Warrensburg, Missouri 64093

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

10.0 out of 10, Exceptional, (8)
"Loved this little home tucked away! "
The price is AU$264
includes taxes & fees
30 Nov - 1 Dec
The Orchard House: Close to the Katy Trail, Truman Lake and Historic Downtown

Hickory Hollow Resort

2.0 star property
8.0 out of 10, Very good, (5)
"The water smells like sewer felt really bad didn't even drink it I hated to shower or worse my face because so smelly stuck up the whole room don't know what was up with it."
The price is AU$356
includes taxes & fees
28 Dec - 29 Dec
Hickory Hollow Resort

CABIN IN THE WOODS , FAMILY AND PET FRIENDLY

9.8 out of 10, Exceptional, (58)
"Did not expect the back ride to be as nice as it was. Lots of fire wood, lots of room to sit around the fire pit and plenty of chair provided. Nicely lit. Lovely back covered deck. Great for grilling and out door dining "
CABIN IN THE WOODS , FAMILY AND PET FRIENDLY

Pet Friendly Lodging 5 minutes from Whiteman AFB

10.0 out of 10, Exceptional, (64)
"The property is easy to find, plenty of parking. It's on a highway, so the traffic is a little loud, but its not terrible. There's a walking path right out front that leads to a state park, and was nice to get our dog out for a walk. The house is comfortable, the main bed is firm (not sagging on both sides). We had to do some switching with pillows, but slept really well."
Pet Friendly Lodging 5 minutes from Whiteman AFB

The Cabin by Bucksaw Marina, Truman Lake

The Cabin by Bucksaw Marina, Truman Lake

Cedar Ridge, 3BR 2 Bath Cabin on Truman Lake

9.8 out of 10, Exceptional, (11)
"Great stay, peaceful and relaxing great for family "
Cedar Ridge, 3BR 2 Bath Cabin on Truman Lake

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

8.8 out of 10, Excellent, (6)
"My Ex husband and I went to visit our son , who is in the Air Force stationed at Whiteman AirForce base. It was really nice and very comfortable. Our son stayed with us and it couldn't have been any better. So much more comfortable than a hotel "
The price is AU$247
includes taxes & fees
1 Dec - 2 Dec
White cabin in the woods close to Univ. of Central Missouri and Whiteman AF Base

Truman Lake Vacation Home on 10 Acres, Borders Public Ground

10.0 out of 10, Exceptional, (51)
"Everything was as listed. Had lots of extras that one might forget at home. The host was easy to get ahold of. Will be returninf"
Truman Lake Vacation Home on 10 Acres, Borders Public Ground

Comfy Newly Furnished Home

9.4 out of 10, Exceptional, (11)
"It was surrounded by everything you needed to do"
Comfy Newly Furnished Home

Pet-Friendly Home in Warsaw w/ Furnished Deck!

7.6 out of 10, Good, (5)
"We arrived and there was no air. 80 degrees in the house. The air conditioner went out and the owner of the property lives out of state and was very attentive to get it fixed. We would recommend this house to anyone that wanted to get away and be way out in the country. Quiet neighborhood and beautiful house!"
Pet-Friendly Home in Warsaw w/ Furnished Deck!

Rm 3 - Waterfront Double Queen / 2nd floor

10.0 out of 10, Exceptional, (2)
"If you ware in the area and need a place to stay this I the place . No matter if it’s for fishing or business these people go out of their way to help you . Me and my wife were down for the weekend to fish and these two thought more than I thought I ever knew about fishing and jigging . They both went out of their way to make our stay memorable he even caught me fresh shad for catfishing . They run a very clean establishment and they take pride in what they do. Thank you both for all you did for...
The price is AU$176
includes taxes & fees
30 Nov - 1 Dec
Rm 3 - Waterfront Double Queen / 2nd floor

Cabin house on a quiet cove - Lake of the Ozarks near Warsaw

10.0 out of 10, Exceptional, (51)
"Beautiful spot"
Cabin house on a quiet cove - Lake of the Ozarks near Warsaw

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

10.0 out of 10, Exceptional, (33)
"The house was clean and pleasant the neighborhood looked sketchy but had no problems"
Lake house with a view! Overlooks Warsaw and Lake of the Ozarks, Sleeps 4

'Lazy RS Lakehouse' w/ Private Hot Tub & Boat Dock

9.8 out of 10, Exceptional, (18)
"Wonderful stay! Owners were easily to access and helpful with any questions. Very responsive. Check out is the EASIEST I’ve had in years of using VRBO. Will book again. "
'Lazy RS Lakehouse' w/ Private Hot Tub & Boat Dock

Cheerful Carefree Cottage with Stunning Lake Views

9.8 out of 10, Exceptional, (53)
"Loved watching the sunset or “show” each night. Just lovely."
Cheerful Carefree Cottage with Stunning Lake Views

Water front Lake of the Ozarks Studio Apartment

10.0 out of 10, Exceptional, (21)
"Stay for a few days, Very quite place, clean and host was friendly."
Water front Lake of the Ozarks Studio Apartment

Warsaw Cabin w/ Sunroom & Lake Access!

9.6 out of 10, Exceptional, (5)
"The propery was very nice. The rooms were great and we loved that there were fans and AC units in all the rooms. The area was decently quiet. We spent most of our time on the screened porch for meals and just hanging out. Love that it was pet friendly and that we could bring our dogs"
Warsaw Cabin w/ Sunroom & Lake Access!
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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Other types of properties in Windsor you may be interested in

Windsor Crossroads Motel

2.5 star property
9.0 out of 10, Wonderful, (75)
"April always provides great service and the rooms are very clean."
The price is AU$109
includes taxes & fees
11 Dec - 12 Dec
Windsor Crossroads Motel

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

9.6 out of 10, Exceptional, (26)
"I wanted an escape to nature. This wasn't it. The newly renovated home/cabin was very clean & convenient inside. Faced directly at another property & backed by a questionable neighborhood. Comfortable, amenities were many. "
The price is AU$243
includes taxes & fees
30 Nov - 1 Dec
Newly remodeled, cozy cottage only steps away from the Katy Trail in Windsor, MO

Econo Lodge Truman Inn

2.0 star property
5.8 out of 10, (607)
"The owner (lady)was very sweet and respectful. Very friendly the room was amazing and smelt very good i will be staying there for now on "
The price is AU$124
includes taxes & fees
1 Dec - 2 Dec
Econo Lodge Truman Inn
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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?

Newly remodeled, cozy cottage only steps away from the Katy Trail in Windsor, MO: This highly rated holiday home rental in Windsor is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. 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.

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 Knob Noster State Park. In the wider area, you’ll find Harry S. Truman State Park and Missouri State Fairgrounds.

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.