Windsor Holiday Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Windsor

Newly remodeled, cozy cottage only steps away from the Katy Trail in Windsor, MO
3 bedrooms, WiFi, bed sheets
Newly remodeled, cozy cottage only steps away from the Katy Trail in Windsor, MO
9.6 out of 10, Exceptional, 22 reviews
"Very quiet and peaceful. We took a nice walk on the Katy Trail. We had the trail all to ourselves. Beautiful in the Fall."
The price is HK$773
per night
23 Jun - 24 Jun
Newly remodeled, cozy cottage only steps away from the Katy Trail in Windsor, MO
Katy Trail Rest Stop
3 bedrooms, WiFi
Katy Trail Rest Stop
9.2 out of 10, Wonderful, 26 reviews
"Great home, has a great time. Was nice to come home and relax after the horse show."
The price is HK$1,132
per night
23 Jun - 24 Jun
Katy Trail Rest Stop
Cheerful Carefree Cottage with Stunning Lake Views
TV, books, video library
Cheerful Carefree Cottage with Stunning Lake Views
9.6 out of 10, Exceptional, 43 reviews
"Absolutely peaceful getaway! We spent the night here for a quiet, unplugged, & peaceful getaway and it did not disappoint. The house was fresh and spotless clean and not overwhelmed with artificial plug-in deodorizers (like many are). While there is a big TV and plenty of movies & games, we literally sat on the screened in porch and enjoyed the view until the sky was dark and again at sunrise. The bird-watching was amazing, we saw a variety including bald eagles. This place goes on our list for...
The price is HK$1,007
per night
20 Jun - 21 Jun
Cheerful Carefree Cottage with Stunning Lake Views
Warsaw Cabin w/ Sunroom & Lake Access!
Exterior
Warsaw Cabin w/ Sunroom & Lake Access!
9.6 out of 10, Exceptional, 4 reviews
"We enjoyed our stay the house and the boat ramp was nice!"
Warsaw Cabin w/ Sunroom & Lake Access!
Looking for a perfect escape from the city !
Fridge, microwave, oven, stovetop
Looking for a perfect escape from the city !
10.0 out of 10, Exceptional, 16 reviews
"Very peaceful just what i was looking for"
The price is HK$1,171
per night
20 Jun - 21 Jun
Looking for a perfect escape from the city !
Lake house with a view! Overlooks Warsaw and Lake of the Ozarks, Sleeps 4
Interior
Lake house with a view! Overlooks Warsaw and Lake of the Ozarks, Sleeps 4
10.0 out of 10, Exceptional, 24 reviews
"Upon entering the house, you notice how good it smells. It's small, cute, cozy, and has the best closed in back porch that is air conditioned for those hot days. The back porch overlooks the lake and you get to catch the absolute perfect sunset! The owners were always so quick in responding to any messages and booking was a breeze! They also thought of everything you might need that you might have forgot (tooth brushes, shampoo/conditioner, snacks if you're getting in late and need some food, a...
Lake house with a view! Overlooks Warsaw and Lake of the Ozarks, Sleeps 4
Downtown Retreat with large privacy fenced yard. Pet Friendly!
Property grounds
Downtown Retreat with large privacy fenced yard. Pet Friendly!
10.0 out of 10, Exceptional, 5 reviews
"we enjoyed our stay. Great location. Love the yard for the dogs to run around. We have stayed here and planned on staying again."
The price is HK$976
per night
23 Jun - 24 Jun
Downtown Retreat with large privacy fenced yard. Pet Friendly!
Tan cabin close to University of Central Missouri and Whiteman AF Base
Fridge, oven, stovetop, coffee/tea maker
Tan cabin close to University of Central Missouri and Whiteman AF Base
10.0 out of 10, Exceptional, 3 reviews
"This is perfect for a quiet place to stay. The owner was very nice and helpful. I will stay here again if i am in the area."
The price is HK$851
per night
20 Jun - 21 Jun
Tan cabin close to University of Central Missouri and Whiteman AF Base
The Reel Retreat- Boat parking, pond, huge porch, close to Truman Lake, WIFI
Fridge, microwave, oven, stovetop
The Reel Retreat- Boat parking, pond, huge porch, close to Truman Lake, WIFI
9.8 out of 10, Exceptional, 20 reviews
"Great home in the country quiet, relaxing, and very clean. We really enjoyed the wrap around deck and outdoor area.Would not hesitate to book again in the future. One of the better homes we have stayed in over the years. Thank you for sharing your beautiful home with us. Mark and Lisa"
The Reel Retreat- Boat parking, pond, huge porch, close to Truman Lake, WIFI
Cabin house on a quiet cove - Lake of the Ozarks near Warsaw
Exterior
Cabin house on a quiet cove - Lake of the Ozarks near Warsaw
10.0 out of 10, Exceptional, 39 reviews
"We have stayed here 2 years in a row and we love it!"
Cabin house on a quiet cove - Lake of the Ozarks near Warsaw
Pet Friendly Lodging 5 minutes from Whiteman AFB
Fridge, microwave, oven, stovetop
Pet Friendly Lodging 5 minutes from Whiteman AFB
10.0 out of 10, Exceptional, 53 reviews
"Having a per friendly place is a definite positive. The place was roomy, quiet and convenient. All we could ask for."
Pet Friendly Lodging 5 minutes from Whiteman AFB
Red cabin close to University of Central Missouri and Whiteman AF Base
Interior
Red cabin close to University of Central Missouri and Whiteman AF Base
10.0 out of 10, Exceptional, 2 reviews
"Perfect for a couple. Great location for peace and quiet. Short drive to Warrensburg for restaurants and shopping. Be sure to visit owner’s store at entrance to property."
The price is HK$703
per night
20 Jun - 21 Jun
Red cabin close to University of Central Missouri and Whiteman AF Base
Hickory Hollow Resort
Private kitchen
Hickory Hollow Resort
2.0 star property
10.0 out of 10, Exceptional, 1 review
"The property was nice and people were very friendly "
The price is HK$730
per night
20 Jun - 21 Jun
Hickory Hollow Resort
Cozy Basement Apartment
Living area
Cozy Basement Apartment
The price is HK$734
per night
20 Jun - 21 Jun
Cozy Basement Apartment
Water front Lake of the Ozarks Studio Apartment
Property grounds
Water front Lake of the Ozarks Studio Apartment
10.0 out of 10, Exceptional, 13 reviews
"It's a fantastic little place to stay great for a weekend or anytime. Kathy is great. All around experience is fantastic we will definitely stay again and again."
Water front Lake of the Ozarks Studio Apartment
Cozy Home w/ Boat Parking 5mins From Truman Dam
Property grounds
Cozy Home w/ Boat Parking 5mins From Truman Dam
9.0 out of 10, Wonderful, 38 reviews
"Very clean and equipped to stay comfortable."
The price is HK$601
per night
24 Jun - 25 Jun
Cozy Home w/ Boat Parking 5mins From Truman Dam
Relax at Grandma’s house with a screened in porch overlooking a private lake!
Property grounds
Relax at Grandma’s house with a screened in porch overlooking a private lake!
10.0 out of 10, Exceptional, 14 reviews
"Small but clean and very welcoming. Just wished it had not stormed and rained us out. Would loved to had more time."
Relax at Grandma’s house with a screened in porch overlooking a private lake!
Cabin on Truman, great for fishing, hunting, or boating. Open for deer season!
Property grounds
Cabin on Truman, great for fishing, hunting, or boating. Open for deer season!
9.4 out of 10, Exceptional, 42 reviews
"Easy place to stay in…. Very remote."
Cabin on Truman, great for fishing, hunting, or boating. Open for deer season!
T's Fish Camp--Sleeps 6-- Extra Boat Parking-- Easy Boat Ramp Access
Exterior
T's Fish Camp--Sleeps 6-- Extra Boat Parking-- Easy Boat Ramp Access
10.0 out of 10, Exceptional, 14 reviews
"This was like staying with close friends. Comfortable, clean and cozy place. Owners stayed upstairs but was never a distraction. Super friendly hosts who wanted to ensure our needs were met. They accommodated our boat parking too. Would certainly recommend this place and we plan to return."
T's Fish Camp--Sleeps 6-- Extra Boat Parking-- Easy Boat Ramp Access
Huge Lakeview|Unique Retreat on Truman Lake|Outdoor Firepit/180°IndoorViews
Outdoor dining
Huge Lakeview|Unique Retreat on Truman Lake|Outdoor Firepit/180°IndoorViews
9.8 out of 10, Exceptional, 50 reviews
"Zero complaints! It is everything you could want and more. If you can’t scratch your lake itch here then it’s not possible."
The price is HK$1,163
per night
11 Jul - 12 Jul
Huge Lakeview|Unique Retreat on Truman Lake|Outdoor Firepit/180°IndoorViews
Don't see what you're looking for?
See all available properties in Windsor
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.

Other types of properties in Windsor you may be interested in

Windsor Crossroads Motel
WiFi
Windsor Crossroads Motel
2.5 star property
9.0 out of 10, Wonderful, 58 reviews
"Simple but good value, and nice staff Great spot for Katy and Rock Island trail riders"
The price is HK$472
per night
30 Jun - 1 Jul
Windsor Crossroads Motel
Newly remodeled, cozy cottage only steps away from the Katy Trail in Windsor, MO
3 bedrooms, WiFi, bed sheets
Newly remodeled, cozy cottage only steps away from the Katy Trail in Windsor, MO
9.6 out of 10, Exceptional, 22 reviews
"Very quiet and peaceful. We took a nice walk on the Katy Trail. We had the trail all to ourselves. Beautiful in the Fall."
The price is HK$773
per night
23 Jun - 24 Jun
Newly remodeled, cozy cottage only steps away from the Katy Trail in Windsor, MO
Econo Lodge Truman Inn
Lobby
Econo Lodge Truman Inn
2.0 star property
5.8 out of 10, 525 reviews
"The staircase was so beautiful. Very enjoyable."
The price is HK$539
per night
1 Jul - 2 Jul
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.

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:

  • View our selection of featured holiday rentals in Windsor
  • Use the map to find apartments and other holiday homes in the Windsor neighbourhood you prefer
  • 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?

Katy Trail Rest Stop: This holiday home rental outside of Windsor has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

What can I see and do in Windsor?

While you're exploring the area, Harry S. Truman State Park and Truman Lake are a couple of picturesque spots to get outside and enjoy nature. In the wider area, you’ll find Missouri State Fairgrounds and Truman Lake Mountain Bike 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.

Recent reviews of Windsor properties
Expedia verified reviews

Parkfield Inn

Parkfield Inn

5/5 Excellent
Mrs
"Very nice motel friendly staff clean "
A verified traveller stayed at Parkfield Inn
Posted 10 hours ago
Parkfield Inn