A river surrounded by autumn-colored trees and rocky terrain.

Ontario Holiday Rentals

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Our top choices for Ontario holiday rentals

1. Private cabin on the beautiful Kickapoo River Valley near Wildcat Mountain Park.

Private cabin on the beautiful Kickapoo River Valley near Wildcat Mountain Park.
Ontario
10.0 out of 10, Exceptional, (6 reviews)
"Great host, beautiful property! Would definitely go back!"
United States
Bridgette B.
The price is NZ$301
includes taxes & fees
8 Sept - 9 Sept
Private cabin on the beautiful Kickapoo River Valley near Wildcat Mountain Park.

2. Cozy, quiet Cabin near Kickapoo River & Wildcat Mountain. Perfect for fisherman.

Cozy, quiet Cabin near Kickapoo River & Wildcat Mountain. Perfect for fisherman.
Ontario
9.8 out of 10, Exceptional, (10 reviews)
"Really nice quiet place. Perfect for our hunting trip. "
United States
Kolin C.
The price is NZ$547
includes taxes & fees
22 Sept - 23 Sept
Cozy, quiet Cabin near Kickapoo River & Wildcat Mountain. Perfect for fisherman.

3. The Rylan a Cozy 1-bedroom cabin in serene Driftless area just outside Viroqua,

The Rylan a Cozy 1-bedroom cabin in serene Driftless area just outside Viroqua,
Viroqua
10.0 out of 10, Exceptional, (1 review)
"It's a great little cabin, perfect if you need a place while exploring the creeks around Viroqua. Exceptionally clean, thoughtfully outfitted, very comfortable. The setting is excellent, and the owner Kathi went out of her way to make me feel welcome. Highly recommended."
United States
Christian H.
The price is NZ$250
includes taxes & fees
21 Sept - 22 Sept
The Rylan a Cozy 1-bedroom cabin in serene Driftless area just outside Viroqua,

4. Hillsboro Driftless Guesthouse is cozy and ready for you!

Hillsboro Driftless Guesthouse is cozy and ready for you!
Hillsboro
10.0 out of 10, Exceptional, (29 reviews)
"The home was extremely clean, decorated nicely, very homey, had everything we needed and more! We can’t wait to return!"
United States
Brett B.
The price is NZ$351
includes taxes & fees
2 Sept - 3 Sept
Hillsboro Driftless Guesthouse is cozy and ready for you!

5. Colorful getaway in friendly Driftless village

Colorful getaway in friendly Driftless village
Wonewoc
10.0 out of 10, Exceptional, (15 reviews)
"It’s a cozy place with all cooking utensils you will ever need! Very comfy beds as well. "
United States
Randy R.
The price is NZ$431
includes taxes & fees
22 Sept - 23 Sept
Colorful getaway in friendly Driftless village

6. Spacious & secluded grand home near Kickapoo River, Bike Trails, & ATV routes

Spacious & secluded grand home near Kickapoo River, Bike Trails, & ATV routes
Norwalk
9.4 out of 10, Exceptional, (30 reviews)
"Everyone had a great time!"
United States
Jim K.
The price is NZ$1,172
includes taxes & fees
1 Sept - 2 Sept
Spacious & secluded grand home near Kickapoo River, Bike Trails, & ATV routes

7. Blakley Hobbit Small Cabin

Blakley Hobbit Small Cabin
Viola
7.6 out of 10, Good, (56 reviews)
"fishing cabin."
United States
joe
The price is NZ$203
includes taxes & fees
2 Sept - 3 Sept
Blakley Hobbit Small Cabin

8. Your adventure begins the second you arrive!

Your adventure begins the second you arrive!
Norwalk
10.0 out of 10, Exceptional, (33 reviews)
"Absolutely wonderful as always will be back"
United States
Chad E.
The price is NZ$349
includes taxes & fees
26 Aug - 27 Aug
Your adventure begins the second you arrive!

9. 6 Bedroom Home in Gods Country

6 Bedroom Home in Gods Country
Wilton
9.8 out of 10, Exceptional, (25 reviews)
"It’s the good house and all the bed rooms have attached bathroom. Suggest to the homeowner is that keeping the bath shower and moisturizer at each room"
United States
Rambabu
The price is NZ$1,165
includes taxes & fees
27 Aug - 28 Aug
6 Bedroom Home in Gods Country

10. Blakley Hobbit Large Cabin

Blakley Hobbit Large Cabin
Viola
8.0 out of 10, Very good, (46 reviews)
"A quiet spot w excellent scenery along the Kickapoo River. Great communication w host & easy check-in/out process."
United States
Rebecca B.
The price is NZ$282
includes taxes & fees
2 Sept - 3 Sept
Blakley Hobbit Large Cabin

11. #10 Blakley Hobbit Campground-Tent spot

#10 Blakley Hobbit Campground-Tent spot
Viola
10.0 out of 10, Exceptional, (3 reviews)
"Great location"
United States
Huan B.
The price is NZ$71
includes taxes & fees
2 Sept - 3 Sept
#10 Blakley Hobbit Campground-Tent spot

12. The Honey Haven

The Honey Haven
Westby
10.0 out of 10, Exceptional, (58 reviews)
"Great place. Perfect location for the Driftless. The host were terrific."
United States
John I.
The price is NZ$420
includes taxes & fees
28 Aug - 29 Aug
The Honey Haven

13. The Incline

The Incline
Norwalk
10.0 out of 10, Exceptional, (7 reviews)
"This place is a perfect couples getaway! "
United States
Kurt T.
The price is NZ$595
includes taxes & fees
23 Sept - 24 Sept
The Incline

14. #4 Blakley Hobbit Campground-Tent spot

#4 Blakley Hobbit Campground-Tent spot
Viola
10.0 out of 10, Exceptional, (2 reviews)
"A great spot for a getaway weekend. 20 minutes to viroqua"
United States
Luke S.
The price is NZ$71
includes taxes & fees
26 Aug - 27 Aug
#4 Blakley Hobbit Campground-Tent spot

15. #9 Blakley Hobbit Campground-Tent spot

#9 Blakley Hobbit Campground-Tent spot
Viola
10.0 out of 10, Exceptional, (1 review)
The price is NZ$71
includes taxes & fees
26 Aug - 27 Aug
#9 Blakley Hobbit Campground-Tent spot

16. Blakley Hobbit Campground-RV spot #4

Blakley Hobbit Campground-RV spot #4
Viola
10.0 out of 10, Exceptional, (1 review)
"Lovely spot right on river. Trout fishing all around area."
United States
Brett
The price is NZ$124
includes taxes & fees
2 Sept - 3 Sept
Blakley Hobbit Campground-RV spot #4

17. #8 Blakley Hobbit Campground-Tent spot

#8 Blakley Hobbit Campground-Tent spot
Viola
9.0 out of 10, Wonderful, (2 reviews)
"We enjoyed the campground very much. A little lacking in facilities but location makes up for it in spades!"
United States
Nicholas B.
The price is NZ$71
includes taxes & fees
26 Aug - 27 Aug
#8 Blakley Hobbit Campground-Tent spot

18. Blakley Hobbit Campground-RV spot #1

Blakley Hobbit Campground-RV spot #1
Viola
9.0 out of 10, Wonderful, (2 reviews)
"Come up several times a year to this location nice mowed grass and close to river."
United States
Paul K.
The price is NZ$124
includes taxes & fees
29 Aug - 30 Aug
Blakley Hobbit Campground-RV spot #1

19. Blakley Hobbit Charming 2-bedroom country house with AC, WiFi in soothing Viola

Blakley Hobbit Charming 2-bedroom country house with AC, WiFi in soothing Viola
Viola
9.2 out of 10, Wonderful, (17 reviews)
"excellent out of the way retreat close to things we wanted to do and great place for us and our cats, the hot tub was a great treat"
United States
Joseph W.
The price is NZ$508
includes taxes & fees
26 Aug - 27 Aug
Blakley Hobbit Charming 2-bedroom country house with AC, WiFi in soothing Viola

20. Cabin on the Kickapoo

Cabin on the Kickapoo
Readstown
9.6 out of 10, Exceptional, (48 reviews)
"Fun little place. Perfect for me and the wife. Close to Kickapoo area hiking. Hot tub was a nice touch to the neat little stay."
United States
Joel M.
The price is NZ$491
includes taxes & fees
2 Sept - 3 Sept
Cabin on the Kickapoo
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 Ontario Hotel Reviews

Find out more about Ontario

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Ontario holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Ontario. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Ontario. Seeing all the best attractions is bound to make you fall in love with Ontario. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Ontario short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Ontario?

Yes, there are holiday rentals close to the most popular sights in Ontario, 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 Ontario has to offer?

Shady Pines Retreat : This highly rated holiday home rental in Ontario is located in a rural location, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals will I find in Ontario?

With 4 Expedia holiday rentals, you're guaranteed to find just the right place for your Ontario stay.

What can I see and do in Ontario?

Kickapoo River and Kickapoo Valley Reserve are a couple of lovely local spots to get outside and enjoy nature. Wildcat Mountain State Park and Mount Pisgah Hemlock-Hardwoods State Natural Area are other places to visit while you're in town.

What are holiday rentals like in Ontario?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Ontario. Holiday rentals offer amenities like WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of seclusion away from shared hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular option for small groups.