Holiday Rentals in Windsor

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Check prices for these dates

Our top choices for Windsor holiday rentals

1. 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, (37 reviews)
"Staying here at the start of a Katy trail bike trip. Stones throw from the trail and perfect house for the overnight. Host super friendly and helpful."
United States
Paul S.
The price is €163
includes taxes & fees
10 Nov - 11 Nov
Newly remodeled, cozy cottage only steps away from the Katy Trail in Windsor, MO

2. Hickory Hollow Resort

Hickory Hollow Resort
2.0 star property
Clinton
8.2 out of 10, Very good, (27 reviews)
"Nice place to stay "
United States
Sam
The price is €104
includes taxes & fees
14 Nov - 15 Nov
Hickory Hollow Resort

3. Red cabin close to University of Central Missouri and Whiteman AF Base

Red cabin close to University of Central Missouri and Whiteman AF Base
Warrensburg
9.6 out of 10, Exceptional, (34 reviews)
"Clean, great communication, and a wonderful spot to stay. Will definitely return."
United States
Kelly
The price is €109
includes taxes & fees
10 Nov - 11 Nov
Red cabin close to University of Central Missouri and Whiteman AF Base

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

Delightful Cabin #4 close to Warrensburg, Knob Knoster, and Clinton.
Warrensburg
9.8 out of 10, Exceptional, (7 reviews)
"I've stayed here twice and will stay again. The owners are friendly and insightful. The property and cabins are very clean."
United States
Sylvia M.
The price is €109
includes taxes & fees
11 Nov - 12 Nov
Delightful Cabin #4 close to Warrensburg, Knob Knoster, and Clinton.

5. Unit B Country home apartment near Warrensburg

Unit B Country home apartment near Warrensburg
Warrensburg
8.8 out of 10, Excellent, (6 reviews)
"Wifi issues, but luckily we were too busy to care. Property was nice and owners were very helpful"
United States
Mary K H.
The price is €109
includes taxes & fees
10 Nov - 11 Nov
Unit B Country home apartment near Warrensburg

6. 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, (19 reviews)
"Excellent stay"
United States
Michael E.
The price is €147
includes taxes & fees
12 Nov - 13 Nov
Blue Cabin in the woods close to Whiteman AF Base and Univ. of Central Missouri

7. Green cabin close to University of Central Missouri and Whiteman AF Base

Green cabin close to University of Central Missouri and Whiteman AF Base
Warrensburg
9.2 out of 10, Wonderful, (21 reviews)
"Immaculate and lovely, check-in was super easy and location perfect."
United States
Sabrina D.
The price is €118
includes taxes & fees
10 Nov - 11 Nov
Green cabin close to University of Central Missouri and Whiteman AF Base

8. 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, (16 reviews)
"This is the best place"
United States
Sergio A.
The price is €147
includes taxes & fees
16 Nov - 17 Nov
White cabin in the woods close to Univ. of Central Missouri and Whiteman AF Base

9. Unit A Country house near Warrensburg

Unit A Country house near Warrensburg
Warrensburg
9.6 out of 10, Exceptional, (5 reviews)
"Everything was exactly as described and the owner was a great host."
United States
leslie f.
The price is €128
includes taxes & fees
3 Dec - 4 Dec
Unit A Country house near Warrensburg

10. Modern 2BR Townhome near the MO State Fair

Modern 2BR Townhome near the MO State Fair
Sedalia
The price is €199
includes taxes & fees
7 Dec - 8 Dec
Modern 2BR Townhome near the MO State Fair

11. Haven House New Comfortable and Clean Retreat

Haven House New Comfortable and Clean Retreat
Sedalia
10.0 out of 10, Exceptional, (41 reviews)
"Our favorite place to stay in Sedalia!"
United States
Cara T.
The price is €171
includes taxes & fees
5 Dec - 6 Dec
Haven House New Comfortable and Clean Retreat

12. Cabin 1 - Reel and Trigger

Cabin 1 - Reel and Trigger
Tom Township
The price is €137
includes taxes & fees
10 Nov - 11 Nov
Cabin 1 - Reel and Trigger

13. Truman Lake Retreat: Relax and Unwind

Truman Lake Retreat: Relax and Unwind
Clinton
10.0 out of 10, Exceptional, (15 reviews)
"A very nice place to stay that was conveniently located to where we spent most of our time."
United States
Jason S.
The price is €440
includes taxes & fees
25 Nov - 26 Nov
Truman Lake Retreat: Relax and Unwind

14. Fisher House Spacious Home in Tiny Home Village

Fisher House Spacious Home in Tiny Home Village
Sedalia
10.0 out of 10, Exceptional, (41 reviews)
"Can’t wait to stay again"
United States
Caleb B.
The price is €168
includes taxes & fees
19 Nov - 20 Nov
Fisher House Spacious Home in Tiny Home Village

15. Truman Lake Retreat: Relax and Unwind

Truman Lake Retreat: Relax and Unwind
3.0 star property
Clinton
The price is €462
includes taxes & fees
25 Nov - 26 Nov
Truman Lake Retreat: Relax and Unwind

16. 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, (14 reviews)
"Great property and a really good location. Very responsive host!"
United States
Jo H.
The price is €172
includes taxes & fees
16 Nov - 17 Nov
Blind Boone Bungalow in the 'Burg– Charming and Stylish 2BR Downtown Retreat

17. Cozy 2BR Home_Sleeps 5_KingBeds_In Warrensburg

Cozy 2BR Home_Sleeps 5_KingBeds_In Warrensburg
Warrensburg
9.4 out of 10, Exceptional, (6 reviews)
"We really enjoyed our stay here and would definitely recommend for couples or small families."
United States
Richard W.
The price is €376
includes taxes & fees
10 Nov - 11 Nov
Cozy 2BR Home_Sleeps 5_KingBeds_In Warrensburg

18. The Gallery - Modern Loft Apartment

The Gallery - Modern Loft Apartment
Sedalia Downtown Historic District
10.0 out of 10, Exceptional, (1 review)
"It was great for the state fair within 2 miles but far enough away it was calm and quite"
United States
Christy M.
The price is €196
includes taxes & fees
10 Nov - 11 Nov
The Gallery - Modern Loft Apartment

19. Walk to State Fairgrounds & Katy Trail, 4BR Home by Park

Walk to State Fairgrounds & Katy Trail, 4BR Home by Park
Sedalia
9.6 out of 10, Exceptional, (8 reviews)
"This is a lovely, spacious home in a great neighborhood. The location is great. It is across the street from a beautiful well-kept park with lots to do!"
United States
Nicki T.
The price is €276
includes taxes & fees
2 Dec - 3 Dec
Walk to State Fairgrounds & Katy Trail, 4BR Home by Park

20. Candlestick Suite

Candlestick Suite
Sedalia Downtown Historic District
10.0 out of 10, Exceptional, (12 reviews)
"Comfortable stay"
United States
David F.
The price is €164
includes taxes & fees
10 Nov - 11 Nov
Candlestick Suite
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.

Find holiday rentals that suit your style

Find out more about Windsor

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, apart-hotels, 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 favorite 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 depends 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 €103 per night. Entering your travel dates in the search wizard you might find 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?

GRANDMA'S GET-A-WAY (Water Front property ) WIFI. Private covered one bay dock.: This holiday home rental outside of Windsor is located on a lake, and has a patio, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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 Harry S. Truman 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.