Orangeville Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Orangeville vacation rentals

A modern kitchen with white cabinets, a wooden island, stainless steel appliances, and a bar stool.

1. Cozy Basement Apartment (700 sq ft) with Full Kitchen

Cozy Basement Apartment (700 sq ft) with Full Kitchen
Orangeville
9.0 out of 10, Wonderful, (2 reviews)
"Great location!"
Canada
Kefa
The price is ￥13,090
￥16,941 total
includes taxes & fees
Nov 14 - Nov 15
Cozy Basement Apartment (700 sq ft) with Full Kitchen
A modern kitchen with a built-in oven, microwave, and stove. There is a dining area with a round table and two chairs. A black sofa and a small side table are in the living area.

2. The Perfect Getaway

The Perfect Getaway
Orangeville
7.8 out of 10, Good, (10 reviews)
"Happy with everything, but we couldn't get any channels on the SmartTV."
Canada
Andrea
The price is ￥19,131
￥33,122 total
includes taxes & fees
Nov 14 - Nov 15
The Perfect Getaway
A two-story brick house with a patio area.

3. Entire place, Ground level walkout Basement with Huge backyard

Entire place, Ground level walkout Basement with Huge backyard
Orangeville
7.4 out of 10, Good, (40 reviews)
"Loved our accommodations! Exactly what we were looking for! Will book next year! Thank you!"
Canada
Darlene M
The price is ￥8,838
￥18,204 total
includes taxes & fees
Dec 6 - Dec 7
Entire place, Ground level walkout Basement with Huge backyard
A deck with two white lounge chairs and a red railing overlooking a lake.

4. Lakeside Private suite (Queen bed room)

Lakeside Private suite (Queen bed room)
Loretto
8.0 out of 10, Very good, (4 reviews)
"We really enjoyed our stay, the place was clean and comfortable. Thank you so much."
Canada
Michael W.
The price is ￥11,188
￥17,320 total
includes taxes & fees
Nov 12 - Nov 13
Lakeside Private suite (Queen bed room)
A room with wooden walls and a bed with a nature-themed duvet.

5. Bright and Cozy Tiny Pine House

Bright and Cozy Tiny Pine House
Erin
8.0 out of 10, Very good, (1 review)
The price is ￥11,188
￥16,056 total
includes taxes & fees
Nov 12 - Nov 13
Bright and Cozy Tiny Pine House
A wooden deck with chairs and tables overlooking a lake, a flag, and a gazebo.

6. Lakeview private suite with kitchen (Twin or King)

Lakeview private suite with kitchen (Twin or King)
Loretto
8.6 out of 10, Excellent, (8 reviews)
"Beautiful spot to stay! Highly recommended "
United States
Patrick S.
The price is ￥13,425
￥21,112 total
includes taxes & fees
Nov 12 - Nov 13
Lakeview private suite with kitchen (Twin or King)
A backyard with a patio, a small shed, and a wooden fence.

7. Studio Apartment in the heart of Caledon

Studio Apartment in the heart of Caledon
CALEDON EAST
8.8 out of 10, Excellent, (8 reviews)
"Beautiful flat !"
Canada
Jaivyn
The price is ￥7,831
￥12,262 total
includes taxes & fees
Nov 17 - Nov 18
Studio Apartment in the heart of Caledon
A wooden deck with chairs and tables overlooking a lake, a flag, and a gazebo.

8. Resort style entire guesthouse with kitchen (2 rooms)

Resort style entire guesthouse with kitchen (2 rooms)
Loretto
5.4 out of 10, (3 reviews)
"Very easy check in "
Canada
Carly C.
The price is ￥19,936
￥27,206 total
includes taxes & fees
Nov 12 - Nov 13
Resort style entire guesthouse with kitchen (2 rooms)
A modern kitchen with white cabinets, stainless steel appliances, and a dining area with a wooden table and chairs.

9. Charming Erin Country House near downtown

Charming Erin Country House near downtown
Erin
7.4 out of 10, Good, (15 reviews)
"Wonderful place. Check in was super easy. Upon entering, everything was very clean with towels and other essentials laid out. House was very beautiful and cozy. "
Canada
Joshveer S.
The price is ￥23,461
￥41,176 total
includes taxes & fees
Nov 16 - Nov 17
Charming Erin Country House near downtown
An aerial view of a riverside property with a large building, a garden, and a small pond.

10. Beautiful Bungalow on Grand River in Fergus.

Beautiful Bungalow on Grand River in Fergus.
Fergus
9.8 out of 10, Exceptional, (30 reviews)
"Great place!"
Canada
Lariska
The price is ￥27,969
￥42,604 total
includes taxes & fees
Nov 19 - Nov 20
Beautiful Bungalow on Grand River in Fergus.
Outdoor dining

11. Peaceful Forest Retreat with Fire Pit and BBQ Near Mansfield Ski Club

Peaceful Forest Retreat with Fire Pit and BBQ Near Mansfield Ski Club
Mulmur
2.0 out of 10, (1 review)
"They double booked and didn’t mention anything till I was able to reach out for check-in and didn’t help with making other plans for where to sleep or refund at all."
Canada
Quinn
The price is ￥25,708
￥45,358 total
includes taxes & fees
Nov 17 - Nov 18
Peaceful Forest Retreat with Fire Pit and BBQ Near Mansfield Ski Club
A modern kitchen with a large island, bar stools, and a view through glass doors to an outdoor patio.

12. Walkout Basement with Private Entrance

Walkout Basement with Private Entrance
Rosedale Village
10.0 out of 10, Exceptional, (6 reviews)
"We had a Great stay and felt very welcome. I would recommend this VRBO."
United States
mark h.
The price is ￥22,375
￥40,834 total
includes taxes & fees
Nov 18 - Nov 19
Walkout Basement with Private Entrance
A neatly made bed with a patterned blanket, a bedside lamp, and a nightstand with a drawer.

13. Modern 2BR Private Suite |Prime Location

Modern 2BR Private Suite |Prime Location
Mayfield West
2.0 out of 10, (1 review)
"The host was asking for more money for no reason"
Canada
Pavit
The price is ￥25,172
￥30,720 total
includes taxes & fees
Nov 13 - Nov 14
Modern 2BR Private Suite |Prime Location
A modern kitchen with a central island, bar stools, stainless steel appliances, and a fireplace.

14. Private Forest Getaway 4BR | Hot Tub & Pond

Private Forest Getaway 4BR | Hot Tub & Pond
Shelburne
The price is ￥65,057
￥110,556 total
includes taxes & fees
Nov 17 - Nov 18
Private Forest Getaway 4BR | Hot Tub & Pond
A modern kitchen with white cabinetry, a central island, and built-in appliances.

15. Caledon Estate

Caledon Estate
CALEDON
7.0 out of 10, Good, (2 reviews)
"Amenities were in extremely bad condition. Poor cleanliness than before. Often a go to spot for us. We invited our family and friends. They were not please with our communication and also on the experience."
United States
Rajesh B.
The price is ￥78,090
￥123,260 total
includes taxes & fees
Nov 12 - Nov 13
Caledon Estate
A wooden staircase with a handrail, leading to a landing with a chandelier.

16. Peaceful country home on 25 acres of wooded land

Peaceful country home on 25 acres of wooded land
Loretto
9.4 out of 10, Exceptional, (3 reviews)
"Check in was easy, the house was a good size to fit my party of 9. It would have been nice if some of the back yard grass was cut to play games and for my small dog. It would help to have a few more towels. The house was clean n comfortable."
Canada
Bev C.
The price is ￥67,686
￥79,266 total
includes taxes & fees
Nov 16 - Nov 17
Peaceful country home on 25 acres of wooded land
Interior

17. The Refresh Stream

The Refresh Stream
Sandalwood West
The price is ￥100,689
￥144,120 total
includes taxes & fees
Nov 16 - Nov 17
The Refresh Stream
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 Orangeville Hotel Reviews

A modern hotel entrance with a prominent sign for Hampton Inn & Suites by Hilton.
Hampton Inn & Suites Orangeville, On

Hampton Inn & Suites Orangeville, On

Hampton Inn & Suites Orangeville, On
Mono

10/10 Excellent

Close to GO station
United States
Patricia
Reviewed August 18, 2026
Hampton Inn & Suites Orangeville, On

Find out more about Orangeville

Search for holiday rentals in Orangeville on Expedia! You can easily find your home rentals, villas, holiday apartments in Orangeville using one of the methods below:

  • View our selection of featured holiday rentals in Orangeville
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  • Enter your travel dates to view the best deals on holiday rentals in Orangeville while they last

Look no further and take a look at our great range of rental properties in Orangeville!

Frequently Asked Questions

Are there vacation rentals in Orangeville?

Yes, we give you a choice of vacation rentals close to the most popular attractions in Orangeville, or you can choose a more secluded option if you want a relaxing place to stay. Orangeville is known for its hockey games and monuments. Make sure you have time to check out the ski areas and sightseeing tours during your trip.

What are some of the best vacation rentals in Orangeville?

Walk to Downtown or conservation area, 2 Bedroom home . Sleeps 4. Pets welcomed: Visitors like this Orangeville vacation home rental. It is located near skiing and has a balcony, a garden, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Orangeville?

Expedia has 12 vacation rentals for your stay in Orangeville.

What’s there to see and do in Orangeville?

Cultural attractions include Theatre Orangeville, whereas Island Lake Conservation Area is a spot to enjoy nature. Orangeville Farmers' Market and Alton Mill Arts Centre are a couple of places you'll find in the larger area.

What’s a vacation rental in Orangeville like?

Vacation rentals are privately owned properties you can stay in for a few weeks or just a few days in Orangeville. Vacation rentals offer amenities like kitchens and laundry facilities so you'll have a home away from home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for a family getaway.