Holiday Rentals in Orangeville

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

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, (9)
"This house is spacious and the perfect location for my stay in Orangeville. I hosted Thanksgiving lunch for 13 people and there were plenty of seats for all. The entrance for this apartment is on the side of the house which isn't mentioned in the description, but the owner was very responsive and I figured it out."
Century home 3 bed with Gas Fireplace/fenced yard and 5 minute walk to Broadway
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
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
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 €675
per night
2 May - 3 May
Amazing Corner Home 6 Bed 3.5 Bath 14 could sleep capacity! Home Away from Home!
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”
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
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 €1,003
per night
2 May - 3 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."
The price is €265
per night
5 May - 6 May
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 €152
per night
2 May - 3 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 €594
per night
2 May - 3 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."
The price is €235
per night
21 May - 22 May
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 €123
per night
2 May - 3 May
Entire place, Ground level walkout Basement with Huge backyard
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 €136
per night
8 May - 9 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...
The price is €311
per night
2 May - 3 May
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 €121
per night
31 May - 1 Jun
Cozy, rustic private studio in the heart of Caledon East next to hiking trails.
Luxury Brampton Mansion
Luxury Brampton Mansion
Hockley Valley River edge Condo #4 - Minutes To Hockley Ski Resort & Winery
The price is €311
per night
2 May - 3 May
Hockley Valley River edge Condo #4 - Minutes To Hockley Ski Resort & Winery
Luxury tiny home on peaceful country estate.
Luxury tiny home on peaceful country estate.
Charming Airbnb Haven @Brampton/Snelgrove !!
The price is €219
per night
31 May - 1 Jun
Charming Airbnb Haven @Brampton/Snelgrove !!
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

Century home 3 bed with Gas Fireplace/fenced yard and 5 minute walk to Broadway
10.0 out of 10, Exceptional, (9)
"This house is spacious and the perfect location for my stay in Orangeville. I hosted Thanksgiving lunch for 13 people and there were plenty of seats for all. The entrance for this apartment is on the side of the house which isn't mentioned in the description, but the owner was very responsive and I figured it out."
Century home 3 bed with Gas Fireplace/fenced yard and 5 minute walk to Broadway
Best Western Plus Orangeville Inn & Suites
2.5 star property
8.8 out of 10, Excellent, (653)
"I loved the walkability of this location!!! The room servuce was fine nothing extraordinary. The only negative was the breakfast potatoes...they tasted like they had been reheated over and over. Everything else tasted good."
The price is €192
per night
16 May - 17 May
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."
The price is €265
per night
5 May - 6 May
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.

Everything you need to know about Orangeville holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Orangeville holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Orangeville holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Orangeville holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Orangeville. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Orangeville holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Orangeville holiday rentals we have selected for you start as low as €121 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Orangeville rentals

At Expedia, we put the best Orangeville holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Orangeville rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Orangeville holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Orangeville. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.

What are some of the best holiday rentals that Orangeville has to offer?

Newly Renovated Basement w/ Private Entrance, 5 mins walk to Headwaters Hospital: This highly rated holiday home rental in Orangeville is located in a rural location, and has a patio, a garden and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 1 hot tub.

How many holiday rentals are there in Orangeville?

Expedia has 6 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