Orangeville Holiday Rentals

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Our top choices for Orangeville holiday rentals

Entire place, Ground level walkout Basement with Huge backyard

Entire place, Ground level walkout Basement with Huge backyard
Orangeville
7.2 out of 10, Good, (24)
"Stayed only for one night unfortunately. Great hosts and they ensured I had everything I needed."
Canada
G B.
The price is NZ$208
includes taxes & fees
16 Dec - 17 Dec
Entire place, Ground level walkout Basement with Huge backyard

The Perfect Getaway

The Perfect Getaway
Orangeville
7.6 out of 10, Good, (5)
"Very clean and tidy. Description not accurate, it says 2 queen beds in each room but there was only 1. Host responded to my questions in a timely manner. I had stated there were 3 guests arriving but we had to ask for more towels, which came fairly quickly. Table is slightly broken but still workable. Futon not comfortable and I had to search for a blanket, no extra sheets for it. Coffee pods were a nice touch although the complementary refreshments consisted of a cream soda, bottle of water and...
United States
Sherry F.
The price is NZ$266
includes taxes & fees
7 Jan - 8 Jan 2026
The Perfect Getaway

Spotless Bright Home By The Headwaters In Orangeville!

Spotless Bright Home By The Headwaters In Orangeville!
Orangeville
8.6 out of 10, Excellent, (9)
"Great place to stay … recommend it "
Canada
Kim A.
The price is NZ$593
includes taxes & fees
5 Jan - 6 Jan 2026
Spotless Bright Home By The Headwaters In Orangeville!

Modern Cozy Getaway

Modern Cozy Getaway
Orangeville
10.0 out of 10, Exceptional, (1)
"It was great "
Canada
Joe
Modern Cozy Getaway

Century home 3 bed with Gas Fireplace/fenced yard and 5 minute walk to Broadway

Century home 3 bed with Gas Fireplace/fenced yard and 5 minute walk to Broadway
Orangeville
10.0 out of 10, Exceptional, (17)
"We had a great stay here, clean, comfortable beds and an attentive host! "
Canada
Jeff P.
Century home 3 bed with Gas Fireplace/fenced yard and 5 minute walk to Broadway

Cozy & Spacious 4BR Orangeville Home w/Patio made for U! 10 min walk to Hospital

Cozy & Spacious 4BR Orangeville Home w/Patio made for U! 10 min walk to Hospital
2.0 star property
Orangeville
Cozy & Spacious 4BR Orangeville Home w/Patio made for U! 10 min walk to Hospital

Newly Reno’d Basement Suite w/ Private Access—10 min walk to Headwaters Hospital

Newly Reno’d Basement Suite w/ Private Access—10 min walk to Headwaters Hospital
Orangeville
9.0 out of 10, Wonderful, (6)
"Very clean and comfortable. Lots of space. "
Canada
Roberta P.
The price is NZ$619
includes taxes & fees
19 Dec - 20 Dec
Newly Reno’d Basement Suite w/ Private Access—10 min walk to Headwaters Hospital

Walk to Downtown or conservation area, 2 Bedroom home . Sleeps 4. Pets welcomed

Walk to Downtown or conservation area, 2 Bedroom home . Sleeps 4. Pets welcomed
Orangeville
10.0 out of 10, Exceptional, (11)
"Great stay"
United States
Bobby B.
Walk to Downtown or conservation area, 2 Bedroom home . Sleeps 4. Pets welcomed

Beautiful Bungalow on Grand River in Fergus.

Beautiful Bungalow on Grand River in Fergus.
Fergus
9.8 out of 10, Exceptional, (20)
"Great space with relaxing settings next to the Grand River"
Canada
Robert
The price is NZ$493
includes taxes & fees
23 Dec - 24 Dec
Beautiful Bungalow on Grand River in Fergus.

Belwood Bunkie Escape & Spa minutes away from Elora

Belwood Bunkie Escape & Spa minutes away from Elora
Belwood
10.0 out of 10, Exceptional, (6)
"Had an absolute wonderful time! Highly recommend this place will definitely come again! "
Canada
Franziska
The price is NZ$301
includes taxes & fees
17 Dec - 18 Dec
Belwood Bunkie Escape & Spa minutes away from Elora

Fall Nordic Cottage Retreat with Hot Tub 60 Minutes from City

Fall Nordic Cottage Retreat with Hot Tub 60 Minutes from City
Caledon
10.0 out of 10, Exceptional, (1)
"Wonderful location, beautiful and lovely in the fall season. Great location for a weekend getaway."
Canada
Jason
The price is NZ$651
includes taxes & fees
16 Dec - 17 Dec
Fall Nordic Cottage Retreat with Hot Tub 60 Minutes from City

Private Room in Brampton- Room 4

Private Room in Brampton- Room 4
Brampton,
The price is NZ$142
includes taxes & fees
22 Dec - 23 Dec
Private Room in Brampton- Room 4

Bright Private Coach House | Above Ground

Bright Private Coach House | Above Ground
Brampton
10.0 out of 10, Exceptional, (3)
"Excellent property."
Canada
Neil
Bright Private Coach House | Above Ground

VRBO 6 Queen Beds in 6 Bedrooms with 3 Bedrooms Having Attached Bath

VRBO 6 Queen Beds in 6 Bedrooms with 3 Bedrooms Having Attached Bath
2.0 star property
Brampton
The price is NZ$989
includes taxes & fees
16 Dec - 17 Dec
VRBO 6 Queen Beds in 6 Bedrooms with 3 Bedrooms Having Attached Bath

Luxury Chic 2BED End Unit in Central Brampton

Luxury Chic 2BED End Unit in Central Brampton
Brampton
2.0 out of 10, (1)
"This unit was not as advertised - nowhere near luxury or chic. Photo was deceiving as unit was way underground and was old and tired. I ended up not staying there at all and forfeited the money I paid! "
Canada
JENNING N.
Luxury Chic 2BED End Unit in Central Brampton

luxurious residence characterized by high-quality materials.

luxurious residence characterized by high-quality materials.
Brampton
6.4 out of 10, (5)
"We enjoyed our stay. Our host was very friendly and communicated with us effectively. She met us upon our arrival and showed us into the apartment. The apartment was beautifully decorated and clean. "
Canada
Holly
The price is NZ$413
includes taxes & fees
16 Dec - 17 Dec
luxurious residence characterized by high-quality materials.

Luxury 5-Bed Home w/ Office & 5 Baths | Peaceful Caledon Escape

Luxury 5-Bed Home w/ Office & 5 Baths | Peaceful Caledon Escape
2.0 star property
caledon
10.0 out of 10, Exceptional, (1)
"The place was spacious and the host was extremely responsive and was very accommodating to all requests! My family and I had an amazing stay and a wonderful experience."
United States
Mathangi S.
Luxury 5-Bed Home w/ Office & 5 Baths | Peaceful Caledon Escape

Luxury Suite

Luxury Suite
Brampton
8.0 out of 10, Very good, (6)
"The name says it all, Luxury Suite. Very nice and comfortable."
Canada
Brian
The price is NZ$246
includes taxes & fees
16 Dec - 17 Dec
Luxury Suite

Gorgeous cozy cottage besides a bustling stream, surrounded by gorgeous greenery

Gorgeous cozy cottage besides a bustling stream, surrounded by gorgeous greenery
Orangeville
8.8 out of 10, Excellent, (15)
"It rained most of the time there so the small cottage seemed to shrink. The scenery outside was beyond wonderful… the stream…the pathways the out building. The hostess was very interesting and gracious."
Canada
Christina R.
Gorgeous cozy cottage besides a bustling stream, surrounded by gorgeous greenery

Beautiful and unique apartment. Quick Access to Greater Toronto Area GTA.

Beautiful and unique apartment. Quick Access to Greater Toronto Area GTA.
Brampton
8.0 out of 10, Very good, (4)
"Pleasant "
United States
Linda S.
The price is NZ$252
includes taxes & fees
16 Dec - 17 Dec
Beautiful and unique apartment. Quick Access to Greater Toronto Area GTA.
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

Find out more about Orangeville

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, 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 NZ$142 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?

Entire place, Ground level walkout Basement with Huge backyard: This highly rated holiday home rental in Orangeville has air conditioning and high-speed Internet access to help you feel perfectly comfortable in your new surroundings. Kitchen amenities such as a fridge and a microwave can make your holiday run smoothly. Our travellers also rate The Perfect Getaway as a favourite home for rent in Orangeville.

How many holiday rentals are there in Orangeville?

Expedia has 11 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. Alton Mill Arts Centre and Hockley Valley Resort 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.