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, 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 AU$237
per night
10 June - 11 June
Newly remodeled, cozy cottage only steps away from the Katy Trail in Windsor, MO
Katy Trail Rest Stop
9.2 out of 10, Wonderful, 25 reviews
"Great home, has a great time. Was nice to come home and relax after the horse show."
The price is AU$337
per night
9 June - 10 June
Katy Trail Rest Stop
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 AU$288
per night
9 June - 10 June
Cheerful Carefree Cottage with Stunning Lake Views
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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 !
10.0 out of 10, Exceptional, 16 reviews
"Very peaceful just what i was looking for"
The price is AU$369
per night
19 June - 20 June
Looking for a perfect escape from the city !
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
New Ranch Home in Heart of Sedalia
9.4 out of 10, Exceptional, 9 reviews
"Great place to stay. Clean, great communication with owner"
New Ranch Home in Heart of Sedalia
Downtown Retreat with large privacy fenced yard. Pet Friendly!
10.0 out of 10, Exceptional, 3 reviews
"Loved our stay. The house was very well stocked with all we could need. Lovely yard to enjoy, close to downtown. Very walkable. Enjoyed our time with family without having to be in a hotel!"
The price is AU$267
per night
23 June - 24 June
Downtown Retreat with large privacy fenced yard. Pet Friendly!
Tan cabin close to University of Central Missouri and Whiteman AF Base
10.0 out of 10, Exceptional, 2 reviews
"Well built cabin! Our stay was comfortable and place is spacious . We liked having a full kitchen and bathroom. Highly recommended!"
The price is AU$209
per night
19 June - 20 June
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
9.8 out of 10, Exceptional, 19 reviews
"This property was like my dream house. The wrap around porch enabled us to set out morning, afternoon and evening regardless of where the sun was. The ceiling fans on the porch kept the bugs away too. The house was super clean and super comfortable. We used the fire pit every night. The only issue we had was our inability to stay longer."
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
10.0 out of 10, Exceptional, 38 reviews
"Enjoyed my stay"
Cabin house on a quiet cove - Lake of the Ozarks near Warsaw
Pet Friendly Lodging 5 minutes from Whiteman AFB
10.0 out of 10, Exceptional, 52 reviews
"Tastefully decorated/furnished with top of the line appliances and wonderfully supplied with everything you can think of or need. Owners great on communication, very hospitable and helpful."
Pet Friendly Lodging 5 minutes from Whiteman AFB
Red cabin close to University of Central Missouri and Whiteman AF Base
10.0 out of 10, Exceptional, 1 review
"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 AU$178
per night
16 June - 17 June
Red cabin close to University of Central Missouri and Whiteman AF Base
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 AU$149
per night
16 June - 17 June
Hickory Hollow Resort
Cozy Basement Apartment
The price is AU$198
per night
16 June - 17 June
Cozy Basement Apartment
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
9.0 out of 10, Wonderful, 38 reviews
"Very clean and equipped to stay comfortable."
The price is AU$275
per night
10 June - 11 June
Cozy Home w/ Boat Parking 5mins From Truman Dam
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!
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
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
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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.

Other types of properties in Windsor you may be interested in

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 AU$100
per night
30 June - 1 July
Windsor Crossroads Motel
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 AU$237
per night
10 June - 11 June
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, 522 reviews
"The staircase was so beautiful. Very enjoyable."
The price is AU$118
per night
1 July - 2 July
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.

Everything you need to know about Windsor holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Windsor holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windsor holiday rentals we have selected for you start as low as AU$149 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Lake house with a view! Overlooks Warsaw and Lake of the Ozarks, Sleeps 4: This holiday home rental outside of Windsor is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

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
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