Orangeville Holiday Rentals

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Check prices for these dates

Tonight
23 Dec - 24 Dec
Tomorrow
24 Dec - 25 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Orangeville holiday rentals

Outdoor dining
Entire place, Ground level walkout Basement with Huge backyard

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, (25)
"Great location Good communication from host Room was a little cool"
Canada
Michael
The price is HK$402
HK$941 total
includes taxes & fees
25 Dec - 26 Dec
Entire place, Ground level walkout Basement with Huge backyard
Interior
The Perfect Getaway

The Perfect Getaway

The Perfect Getaway
Orangeville
7.6 out of 10, Good, (5)
"This place was perfect for us attending a wedding nearby . The place was spotless, enough clean towels , water in fridge , cookies, coffee pods , Ketchup and condiment pkgs in the fridge.A very thoughtful host, thought of everything.Whilst booking i had a few questions and Britney answered them in a timely manner.Loved our stay . Would go back again if in the area in a heartbeat "
United States
Catherine S.
The price is HK$625
HK$1,207 total
includes taxes & fees
7 Jan - 8 Jan 2026
The Perfect Getaway
Interior
Spotless Bright Home By The Headwaters In Orangeville!

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 HK$1,136
HK$2,562 total
includes taxes & fees
5 Jan - 6 Jan 2026
Spotless Bright Home By The Headwaters In Orangeville!
Outdoor dining
Studio Apartment in the heart of Caledon

Studio Apartment in the heart of Caledon

Studio Apartment in the heart of Caledon
CALEDON EAST
8.6 out of 10, Excellent, (4)
"Beautiful flat !"
Canada
Jaivyn
The price is HK$396
HK$691 total
includes taxes & fees
29 Dec - 30 Dec
Studio Apartment in the heart of Caledon
Property grounds
Belwood Bunkie Escape & Spa minutes away from Elora

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 HK$764
HK$1,362 total
includes taxes & fees
30 Dec - 31 Dec
Belwood Bunkie Escape & Spa minutes away from Elora
1 bedroom, WiFi, bed sheets
Private Room in Brampton- Room 4

Private Room in Brampton- Room 4

Private Room in Brampton- Room 4
Brampton,
The price is HK$326
HK$643 total
includes taxes & fees
6 Jan - 7 Jan 2026
Private Room in Brampton- Room 4
Terrace/patio
Lakeside Private suite (Queen bed room)

Lakeside Private suite (Queen bed room)

Lakeside Private suite (Queen bed room)
Loretto
The price is HK$543
HK$921 total
includes taxes & fees
26 Dec - 27 Dec
Lakeside Private suite (Queen bed room)
Interior
The Refresh Stream

The Refresh Stream

The Refresh Stream
Brampton
The price is HK$713
HK$2,020 total
includes taxes & fees
25 Dec - 26 Dec
The Refresh Stream
Exterior
Luxury Suite

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
Luxury Suite
1 bedroom, iron/ironing board, WiFi, bed sheets
Cozy One-bedroom Walkout Apartment with Living Area & full kitchen- Entire Home

Cozy One-bedroom Walkout Apartment with Living Area & full kitchen- Entire Home

Cozy One-bedroom Walkout Apartment with Living Area & full kitchen- Entire Home
2.0 star property
Brampton
The price is HK$493
HK$960 total
includes taxes & fees
25 Dec - 26 Dec
Cozy One-bedroom Walkout Apartment with Living Area & full kitchen- Entire Home
Private kitchen
Fully private basement

Fully private basement

Fully private basement
2.0 star property
Brampton
The price is HK$659
HK$925 total
includes taxes & fees
7 Jan - 8 Jan 2026
Fully private basement
Interior
Beautiful and unique apartment. Quick Access to Greater Toronto Area GTA.

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 HK$679
HK$1,138 total
includes taxes & fees
25 Dec - 26 Dec
Beautiful and unique apartment. Quick Access to Greater Toronto Area GTA.
Fridge, microwave, oven, stovetop
Walkout Basement with Private Entrance

Walkout Basement with Private Entrance

Walkout Basement with Private Entrance
Brampton
10.0 out of 10, Exceptional, (6)
"Lovely private basement apartment. We particularly enjoyed the outdoor patio. Hosts were friendly and helpful. "
United States
Janice C.
The price is HK$1,018
HK$1,758 total
includes taxes & fees
6 Jan - 7 Jan 2026
Walkout Basement with Private Entrance
1 bedroom, bed sheets
Bright and Cozy Tiny Pine House

Bright and Cozy Tiny Pine House

Bright and Cozy Tiny Pine House
Erin
The price is HK$566
HK$914 total
includes taxes & fees
31 Dec - 1 Jan 2026
Bright and Cozy Tiny Pine House
Dining
Fall Nordic Cottage Retreat with Hot Tub 60 Minutes from City

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, (2)
"Would recommend, great spot."
Canada
Tim S.
Fall Nordic Cottage Retreat with Hot Tub 60 Minutes from City
Exterior
Cozy 2-Bedroom Retreat with Private Bath

Cozy 2-Bedroom Retreat with Private Bath

Cozy 2-Bedroom Retreat with Private Bath
Erin
The price is HK$861
HK$1,401 total
includes taxes & fees
25 Dec - 26 Dec
Cozy 2-Bedroom Retreat with Private Bath
Interior
Beautiful New Build by Elora

Beautiful New Build by Elora

Beautiful New Build by Elora
Fergus
8.0 out of 10, Very good, (14)
"Great place to stay!"
United States
Joey M.
The price is HK$962
HK$2,258 total
includes taxes & fees
19 Jan - 20 Jan 2026
Beautiful New Build by Elora
Exterior
Fastbear 2

Fastbear 2

Fastbear 2
Brampton
The price is HK$1,075
HK$2,775 total
includes taxes & fees
25 Dec - 26 Dec
Fastbear 2
Exterior
Spacious 3BR Home | Sleeps 8 | Central Brampton

Spacious 3BR Home | Sleeps 8 | Central Brampton

Spacious 3BR Home | Sleeps 8 | Central Brampton
2.0 star property
Brampton
The price is HK$955
HK$2,183 total
includes taxes & fees
28 Dec - 29 Dec
Spacious 3BR Home | Sleeps 8 | Central Brampton
Exterior
Beautiful Bungalow on Grand River in Fergus.

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 HK$1,415
HK$2,270 total
includes taxes & fees
2 Jan - 3 Jan 2026
Beautiful Bungalow on Grand River in Fergus.
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

Hampton Inn & Suites Orangeville, On

Hampton Inn & Suites Orangeville, On

10/10 Excellent
"Everything was great. "
louie 1-night trip
Posted 2 days ago
Hampton Inn & Suites Orangeville, On

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 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.