Orangeville Holiday Rentals

Save an average of 15% on thousands of properties with Expedia Rewards

Most properties are fully refundable. Because flexibility matters.

Search over 2.9 million properties and 550 airlines worldwide

Holiday Rentals in Orangeville

Fully Furnished 2 Bedroom home . Sleeps 4. Pets welcomed
10.0 out of 10, Exceptional, (5)
"The property was well and efficiently laid out, which made it even more inviting than the pictures suggested it would be. Excellent for entertaining (had family visit for dinner one evening). The welcome kit was a thoughtful and welcome addition. In summer, I would have greatly enjoyed the balcony off the main bedroom. The age of the property added a feeling of grandeur that was much appreciated, and, as one who grew up in Orangeville, the location of the property, between the historic charm of...
Fully Furnished 2 Bedroom home . Sleeps 4. Pets welcomed
Century home 3 bed with Gas Fireplace/fenced yard and 5 minute walk to Broadway
10.0 out of 10, Exceptional, (10)
"The facilities are spacious. We came with four adults and were quite comfortable. The owner bent over backwards to make our stay excellent. Thanks for his attention to everything."
Century home 3 bed with Gas Fireplace/fenced yard and 5 minute walk to Broadway
A bright & modern urban studio
10.0 out of 10, Exceptional, (5)
"Had a great stay bed was very comfortable the shower was great and had amazing water pressure. This was very central for me visiting with my family. Thanks Andrew & Amee"
A bright & modern urban studio
Save an average of 15% on thousands of hotels when you're signed in
Hockley “Hidden Treasure”
10.0 out of 10, Exceptional, (14)
"The property exceeded expectations in every way and was the perfect weekend getaway spot for our family of 8 adults and one toddler. We took full advantage of the three large gathering areas and also the extras which were totally set up for us including a hot tub and large fire pit area. We also found very good trails and dining nearby and the hostess was very responsive and helpful throughout the weekend. Highly recommend this property."
Hockley “Hidden Treasure”
Paradise Suites - Peaceful Getaway
10.0 out of 10, Exceptional, (3)
"We enjoyed this house very much. House was very clean and well furnished. I highly recommend this house."
The price is NZ$1,211
per night
16 May - 17 May
Paradise Suites - Peaceful Getaway
Charming Rural Getaway - close to hiking and skiing
10.0 out of 10, Exceptional, (66)
"Taria was a fantastic host and ensured I had everything I needed during my stay. Would highly recommend this property to anyone looking for rest and relaxation. Excited to stay again when the weather warms up a bit so I can explore the area and enjoy everything it has to offer. Pet friendly too which was a definite bonus. I couldn't have asked for a better mini vacation! Thanks again!"
Charming Rural Getaway - close to hiking and skiing
Amazing Corner Home 6 Bed 3.5 Bath 14 could sleep capacity! Home Away from Home!
10.0 out of 10, Exceptional, (4)
"Booked last minute with Jahnavi after my other booking was cancelled on me on the day I was supposed to check in. Jahnavi was extremely accommodating in allowing me to do a same day booking. He was very responsive and his place was in amazing condition. We had a gathering to celebrate my boyfriend’s birthday, and everyone had an amazing time !! Would definitely book again :)"
The price is NZ$1,173
per night
16 May - 17 May
Amazing Corner Home 6 Bed 3.5 Bath 14 could sleep capacity! Home Away from Home!
The Blue Cottage Experience
10.0 out of 10, Exceptional, (2)
"Our stay was amazing. The place was super clean and spacious. Very lovely interior and exterior. Host was extremely communicative. 10/10. If I had any criticism, it would be that some of the beds were a little stiff. Aside from that, I HIGHLY recommend this place."
The Blue Cottage Experience
Hockley Riverside Cottage • Loft & Bunkie
10.0 out of 10, Exceptional, (12)
"We had a wonderful time at this property and it was perfect gateway experience. Being close to the river was so relaxing and everything about the place was unforgettable memory got us! Highly recommended."
Hockley Riverside Cottage • Loft & Bunkie
Luxurious home for retreat - 5 minutes to Elora, 15 minutes to Guelph
10.0 out of 10, Exceptional, (1)
Luxurious home for retreat - 5 minutes to Elora, 15 minutes to Guelph
Log house with pool! Close to Toronto! 5 mins from downtown Bolton!
9.0 out of 10, Wonderful, (2)
"The property was beautiful and peaceful and the owners were incredibly nice"
The price is NZ$1,761
per night
16 May - 17 May
Log house with pool! Close to Toronto! 5 mins from downtown Bolton!
Newly Renovated Basement w/ Private Entrance, 5 mins walk to Headwaters Hospital
8.6 out of 10, Excellent, (4)
"Orangeville is a great town, this property is located SE side of town near the hospital but great easy access to town. Property Manager was very easy to get a hold of no major issues for our stay. I do suggest bringing paper towels or napkins was not able to locate on the property."
Newly Renovated Basement w/ Private Entrance, 5 mins walk to Headwaters Hospital
Luxury Suite
8.0 out of 10, Very good, (3)
"Property was clean and as advertised. Two nice sized bedrooms with a full kitchen and bathroom. Check-in was fast and convenient. Quiet neighbourhood."
The price is NZ$263
per night
16 May - 17 May
Luxury Suite
Mesmerizing 6 Bed 3.5 Bath Home - Open Concept Kitchen Living Dining & Parkings
8.0 out of 10, Very good, (1)
"First time ever using Vrbo. All goes well until a week after my stay is over. Owner decides (suddenly) to try to bill me over $1100 for an alleged broken bed. After I had travelled and find myself back home in my country. Just when I thought it all went well. And I have no way to know if someone else did this after I left or if this is even true."
The price is NZ$1,033
per night
16 May - 17 May
Mesmerizing 6 Bed 3.5 Bath Home - Open Concept Kitchen Living Dining & Parkings
Cozy Basement w/ Private Entrance & Outdoor Basketball Court — Close to Brampton
8.0 out of 10, Very good, (7)
"My collogues and I had a Great Stay. We were very comfortable and felt safe. The Local attractions we very easy to get to."
Cozy Basement w/ Private Entrance & Outdoor Basketball Court — Close to Brampton
Entire place, Ground level walkout Basement with Huge backyard
7.4 out of 10, Good, (10)
"FURNACE motor very loud. No cloth hangers. Bring your own I guess. "
The price is NZ$211
per night
16 May - 17 May
Entire place, Ground level walkout Basement with Huge backyard
Oh Canada! Home Away from Home!! Every Moment Comfortable and Enjoyable Stay!!!
6.0 out of 10, (2)
"Very nice place. Had everything that we needed. Would stay again and recommend to others. Thank RR"
The price is NZ$1,173
per night
18 May - 19 May
Oh Canada! Home Away from Home!! Every Moment Comfortable and Enjoyable Stay!!!
Entire top floor huge 1 bedroom apt private entry!
5.4 out of 10, (3)
"The house was clean and the host was very accommodating!"
The price is NZ$234
per night
28 May - 29 May
Entire top floor huge 1 bedroom apt private entry!
Luxury 2 bedroom 2 full baths rooms
4.0 star property
5.0 out of 10, (4)
"THIS IS A FRAUDULENT LISTING. Don't waste your time and money by booking this property.Unfortuanately I fell into the trap by booking this....got a call from the owner just few hours before the check-in time and was told that someone else has booked the place and my reservation did not go through even though my payment was processed through Expedia. The owner gave some lame excuse and clearly was a cheater. Expedia made an alternative arrangement since they were not able to make contact and was...
Luxury 2 bedroom 2 full baths rooms
Cozy, rustic private studio in the heart of Caledon East next to hiking trails.
4.0 out of 10, (1)
The price is NZ$208
per night
31 May - 1 Jun
Cozy, rustic private studio in the heart of Caledon East next to hiking trails.
Don't see what you're looking for?
See all available properties in Orangeville
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 Orangeville you may be interested in

Fully Furnished 2 Bedroom home . Sleeps 4. Pets welcomed
10.0 out of 10, Exceptional, (5)
"The property was well and efficiently laid out, which made it even more inviting than the pictures suggested it would be. Excellent for entertaining (had family visit for dinner one evening). The welcome kit was a thoughtful and welcome addition. In summer, I would have greatly enjoyed the balcony off the main bedroom. The age of the property added a feeling of grandeur that was much appreciated, and, as one who grew up in Orangeville, the location of the property, between the historic charm of...
Fully Furnished 2 Bedroom home . Sleeps 4. Pets welcomed
Best Western Plus Orangeville Inn & Suites
2.5 star property
8.6 out of 10, Excellent, (658)
"My family lives in Orangeville. I stay at this hotel every time I visit. We usually get a good, quiet room with a nice view. This particular trip our room is noisy (right next to the elevator and ice machine) and our view is a view of the roof. The towels look used and refolded. We are extremely disappointed. "
The price is NZ$342
per night
9 Jun - 10 Jun
Best Western Plus Orangeville Inn & Suites
Newly Renovated Basement w/ Private Entrance, 5 mins walk to Headwaters Hospital
8.6 out of 10, Excellent, (4)
"Orangeville is a great town, this property is located SE side of town near the hospital but great easy access to town. Property Manager was very easy to get a hold of no major issues for our stay. I do suggest bringing paper towels or napkins was not able to locate on the property."
Newly Renovated Basement w/ Private Entrance, 5 mins walk to Headwaters Hospital
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.

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 Orangeville 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 Orangeville. 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 Orangeville. Seeing all the best attractions is bound to make you fall in love with Orangeville. 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 Orangeville short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Orangeville?

Yes, there are holiday rentals close to the most popular sights in Orangeville, or you can select a more secluded option if you're looking for a relaxing 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.

How many holiday rentals are there in Orangeville?

Expedia has 7 holiday 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. Hockley Valley Resort and Osprey Valley Golf are a couple of places you'll find in the wider area.

What’s a holiday rental in Orangeville like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Orangeville. Holiday rentals provide amenities such as laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and busy front desks while still allowing you the experience of travel. You'll also have 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 Orangeville properties
Expedia verified reviews