A cityscape with a mix of historic and modern buildings, a parking lot, and a river in the background.

Orangeville Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Orangeville vacation rentals

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.

1. The Perfect Getaway

The Perfect Getaway
Orangeville
7.8 out of 10, Good, (9 reviews)
"britney was great.she put one more bed for us so we can all sleep cpmfprtably.the loction os great.it was nice and cozy"
Canada
???? ?.
The price is ￥20,205
￥36,023 total
includes taxes & fees
Oct 9 - Oct 10
The Perfect Getaway
A two-story brick house with a patio area.

2. 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)
"This place needs lots of upgrades and no privacy at all. No blinds for the widows front door is unsecured. Needs more lights."
Canada
Nilantha
The price is ￥7,981
￥18,658 total
includes taxes & fees
Sep 30 - Oct 1
Entire place, Ground level walkout Basement with Huge backyard
A modern kitchen with white cabinets, a wooden island, stainless steel appliances, and a bar stool.

3. 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 ￥14,592
￥18,011 total
includes taxes & fees
Oct 17 - Oct 18
Cozy Basement Apartment (700 sq ft) with Full Kitchen
A spiral staircase with wooden handrails and carpeted steps.

4. Spacious 4BR Orangeville Home, Private Deck, Sleeps 10—Near Headwaters Hospital!

Spacious 4BR Orangeville Home, Private Deck, Sleeps 10—Near Headwaters Hospital!
Orangeville
The price is ￥24,919
￥59,615 total
includes taxes & fees
Sep 27 - Sep 28
Spacious 4BR Orangeville Home, Private Deck, Sleeps 10—Near Headwaters Hospital!
A wooden cabin with a fire pit and string lights, surrounded by trees.

5. Cozy Belwood Bunkie Retreat - 10 Min to Elora Gorge

Cozy Belwood Bunkie Retreat - 10 Min to Elora Gorge
Belwood
9.4 out of 10, Exceptional, (21 reviews)
"The cabin was perfect"
Canada
Siddharth
The price is ￥18,184
￥30,822 total
includes taxes & fees
Sep 28 - Sep 29
Cozy Belwood Bunkie Retreat - 10 Min to Elora Gorge
A modern kitchen with white cabinetry, a central island, and built-in appliances.

6. 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 ￥78,349
￥130,138 total
includes taxes & fees
Sep 25 - Sep 26
Caledon Estate
A deck with two white lounge chairs and a red railing overlooking a lake.

7. Lakeside Private suite (Queen bed room)

Lakeside Private suite (Queen bed room)
Loretto
8.0 out of 10, Very good, (3 reviews)
"We really enjoyed our stay, the place was clean and comfortable. Thank you so much."
Canada
Michael W.
The price is ￥11,225
￥18,773 total
includes taxes & fees
Sep 27 - Sep 28
Lakeside Private suite (Queen bed room)
A modern kitchen with white cabinets, stainless steel appliances, and a dining area with a wooden table and chairs.

8. Charming Erin Country House near downtown

Charming Erin Country House near downtown
Erin
7.4 out of 10, Good, (13 reviews)
"Beautiful home, very clean and comfortable. Would definitely stay again!"
Canada
Nancy B.
The price is ￥24,751
￥44,966 total
includes taxes & fees
Sep 29 - Sep 30
Charming Erin Country House near downtown
A wooden staircase with a handrail, leading to a landing with a chandelier.

9. Peaceful country home on 25 acres of wooded land

Peaceful country home on 25 acres of wooded land
Loretto
8.0 out of 10, Very good, (1 review)
"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 ￥67,910
￥87,520 total
includes taxes & fees
Sep 28 - Sep 29
Peaceful country home on 25 acres of wooded land
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, (27 reviews)
"The property was beautifully kept and very easy communication with the owner. I would recommend this place to anyone wanting to stay in the Fergus area. "
Canada
Aubrey B.
The price is ￥28,062
￥44,901 total
includes taxes & fees
Sep 28 - Sep 29
Beautiful Bungalow on Grand River in Fergus.
A room with wooden walls and a bed with a nature-themed duvet.

11. 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 ￥11,225
￥17,504 total
includes taxes & fees
Sep 28 - Sep 29
Bright and Cozy Tiny Pine House
A hot tub on a wooden deck with a metal railing, surrounded by a grassy yard and trees.

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

Private Forest Getaway 4BR | Hot Tub & Pond
Shelburne
The price is ￥61,193
￥100,163 total
includes taxes & fees
Sep 29 - Sep 30
Private Forest Getaway 4BR | Hot Tub & Pond

13. The Refresh Stream

The Refresh Stream
Sandalwood West
The price is ￥101,023
￥148,149 total
includes taxes & fees
Sep 29 - Sep 30
The Refresh Stream
A backyard with a patio, a small shed, and a wooden fence.

14. Studio Apartment in the heart of Caledon

Studio Apartment in the heart of Caledon
CALEDON EAST
8.4 out of 10, Very good, (6 reviews)
"Beautiful flat !"
Canada
Jaivyn
The price is ￥7,857
￥11,162 total
includes taxes & fees
Oct 8 - Oct 9
Studio Apartment in the heart of Caledon
A neatly made bed with a patterned blanket, a bedside lamp, and a nightstand with a drawer.

15. 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 ￥23,853
￥30,506 total
includes taxes & fees
Sep 25 - Sep 26
Modern 2BR Private Suite |Prime Location
A modern kitchen with a large island, bar stools, and a view through glass doors to an outdoor patio.

16. 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 ￥20,205
￥40,462 total
includes taxes & fees
Oct 21 - Oct 22
Walkout Basement with Private Entrance
A wooden deck with chairs and tables overlooking a lake, a flag, and a gazebo.

17. 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 ￥20,003
￥28,819 total
includes taxes & fees
Sep 27 - Sep 28
Resort style entire guesthouse with kitchen (2 rooms)
A wooden deck with chairs and tables overlooking a lake, a flag, and a gazebo.

18. 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 ￥13,470
￥22,578 total
includes taxes & fees
Oct 1 - Oct 2
Lakeview private suite with kitchen (Twin or King)
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

Best Western Plus Orangeville Inn & Suites

Best Western Plus Orangeville Inn & Suites

10/10 Excellent
"Great, Clean place. I’d recommend it."
Christine 1-night trip
Posted 3 hours ago
Best Western Plus Orangeville Inn & Suites

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
  • Use the map to find apartments and other holiday homes in the Orangeville neighbourhood you prefer
  • 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?

Charming Erin Country House near downtown: You might want to consider this vacation home rental near Orangeville, which is equipped with a garden, air-conditioning, and laundry facilities to help you feel comfortable during your stay. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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 Hockley Valley Resort 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.