Orangeville Holiday Rentals

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Holiday Rentals in Orangeville

Century home 3 bed with Gas Fireplace/fenced yard and 5 minute walk to Broadway
10.0 out of 10, Exceptional, 10 reviews
"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 reviews
"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
Newly Renovated Basement w/ Private Entrance, 5 mins walk to Headwaters Hospital
8.6 out of 10, Excellent, 4 reviews
"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
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Fully Furnished 2 Bedroom home . Sleeps 4. Pets welcomed
10.0 out of 10, Exceptional, 6 reviews
"Perfect location in Orangeville. Walkable to the main street and easy access to highways/other roads/attractions in the area. Dog and family friendly - exactly what we're looking for. Great host that was easy to communicate with pre and during."
Fully Furnished 2 Bedroom home . Sleeps 4. Pets welcomed
Entire place, Ground level walkout Basement with Huge backyard
7.4 out of 10, Good, 10 reviews
"FURNACE motor very loud. No cloth hangers. Bring your own I guess. "
The price is NZ$208
per night
8 Jun - 9 Jun
Entire place, Ground level walkout Basement with Huge backyard
Entire top floor huge 1 bedroom apt private entry!
5.4 out of 10, 3 reviews
"The house was clean and the host was very accommodating!"
The price is NZ$231
per night
3 Jul - 4 Jul
Entire top floor huge 1 bedroom apt private entry!
Charming Rural Getaway - close to hiking and skiing
10.0 out of 10, Exceptional, 68 reviews
"This place was the perfect stay for us. Lots of things to do on the property and the cottage is stocked with anything you could need. I appreciated the quick and friendly communication from the host. Would definitely recommend to any couples looking for a getaway!"
Charming Rural Getaway - close to hiking and skiing
Paradise Suites - Peaceful Getaway
10.0 out of 10, Exceptional, 3 reviews
"We enjoyed this house very much. House was very clean and well furnished. I highly recommend this house."
The price is NZ$1,617
per night
4 Jun - 5 Jun
Paradise Suites - Peaceful Getaway
Specious 4 Bedroom ~ 3.5 Washroom ~ Brand New ~ Caledon
Specious 4 Bedroom ~ 3.5 Washroom ~ Brand New ~ Caledon
Heartlake Oasis Revine View- Walkout Basement
The price is NZ$346
per night
4 Jun - 5 Jun
Heartlake Oasis Revine View- Walkout Basement
Hockley “Hidden Treasure”
10.0 out of 10, Exceptional, 15 reviews
"We work remotely from our homes doing Personal taxes, January till May, each year. We meet in person on Victoria Day weekend …this was our 3rd sync up …NFalls and Montreal… were the first 2 The property was better than the pictures…pictures cannot describe how comfortable you can get with the sound of the stream in the morning, and the crackle of a fire at night …we will , should you accept, be reserving same weekend next year … Place is a treasure Host was a pleasure"
Hockley “Hidden Treasure”
Luxury tiny home on peaceful country estate.
Luxury tiny home on peaceful country estate.
Cozy, rustic private studio in the heart of Caledon East next to hiking trails.
4.0 out of 10, 1 review
The price is NZ$205
per night
20 Jun - 21 Jun
Cozy, rustic private studio in the heart of Caledon East next to hiking trails.
Luxury 2 bedroom 2 full baths rooms
4.0 star property
5.0 out of 10, 4 reviews
"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
Amazing Corner Home 6 Bed 3.5 Bath 14 could sleep capacity! Home Away from Home!
10.0 out of 10, Exceptional, 4 reviews
"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$1,153
per night
4 Jun - 5 Jun
Amazing Corner Home 6 Bed 3.5 Bath 14 could sleep capacity! Home Away from Home!
Charming Airbnb Haven @Brampton/Snelgrove !!
The price is NZ$383
per night
8 Jun - 9 Jun
Charming Airbnb Haven @Brampton/Snelgrove !!
2 bedroom legal basement apartment with full bath, including private entrance
The price is NZ$247
per night
4 Jun - 5 Jun
2 bedroom legal basement apartment with full bath, including private entrance
Centreville Suites - Peaceful 10+ Acre Getaway
Centreville Suites - Peaceful 10+ Acre Getaway
Beautiful and unique apartment. Quick Access to Greater Toronto Area GTA.
8.0 out of 10, Very good, 1 review
"Lot of noise over my head on sunday night,cause this was a basement"
The price is NZ$239
per night
4 Jun - 5 Jun
Beautiful and unique apartment. Quick Access to Greater Toronto Area GTA.
Amazing Fun Place With 6 Beds 3.5 Bath Home Having 14 People Sleeping Capacity
The price is NZ$1,230
per night
4 Jun - 5 Jun
Amazing Fun Place With 6 Beds 3.5 Bath Home Having 14 People Sleeping Capacity
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

Best Western Plus Orangeville Inn & Suites
2.5 star property
8.6 out of 10, Excellent, 664 reviews
"Room decor is a little dated and needs repair (wall paper) and better lighting. Service is great and breakfast options are good. "
The price is NZ$337
per night
16 Jun - 17 Jun
Best Western Plus Orangeville Inn & Suites
Atlanta Motel
2.0 star property
6.8 out of 10, 128 reviews
"A hook or towel bar near the shower would have been very convenient."
Atlanta Motel
Newly Renovated Basement w/ Private Entrance, 5 mins walk to Headwaters Hospital
8.6 out of 10, Excellent, 4 reviews
"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