Book Holiday Homes in Orangeville

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Orangeville

Credit River Cottage, A rustic 4-season sanctuary in Inglewood, Caledon.

Credit River Cottage, A rustic 4-season sanctuary in Inglewood, Caledon.

Inglewood ON
When you stay at this vacation home in Caledon, you'll be next to a golf course, within a 5-minute drive of Caledon Country Club and Cheltenham Badlands.
Opens in a new windowCredit River Cottage, A rustic 4-season sanctuary in Inglewood, Caledon.
Luxury 5-Bed Home w/ Office & 5 Baths | Peaceful Caledon Escape

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

caledon ON
With a stay at this vacation home in Caledon, you'll be within a 10-minute drive of Royal Ambassador Banquet and Plant Paradise Country Gardens.
Opens in a new windowLuxury 5-Bed Home w/ Office & 5 Baths | Peaceful Caledon Escape
Entire place, Ground level walkout Basement  with Huge backyard

Entire place, Ground level walkout Basement with Huge backyard

Orangeville ON
The price is AU$177 per night from 31 Mar to 1 Apr
AU$177
31 Mar - 1 Apr
includes taxes & fees
Located in Orangeville, this vacation home is a 4-minute drive from Theatre Orangeville and 6 minutes from Island Lake Conservation Area.
Opens in a new windowEntire place, Ground level walkout Basement with Huge backyard
Save an average of 15% on thousands of hotels when you're signed in
Cozy One bedroom suite 5min to Orangeville Downtown

Cozy One bedroom suite 5min to Orangeville Downtown

Orangeville ON
The price is AU$215 per night from 31 Mar to 1 Apr
AU$215
31 Mar - 1 Apr
includes taxes & fees
A stay at this vacation home places you in the heart of Orangeville, within a 5-minute drive of Island Lake Conservation Area and Theatre Orangeville.
Opens in a new windowCozy One bedroom suite 5min to Orangeville Downtown
Ravine Getaway | Family & Wedding Retreat – Sleeps 20, 3 Kitchens, Nature Views

Ravine Getaway | Family & Wedding Retreat – Sleeps 20, 3 Kitchens, Nature Views

Brampton ON
Located in Brampton, this vacation home is on a river, within a 5-minute drive of Heart Lake Conservation Area and Heart Lake.
Opens in a new windowRavine Getaway | Family & Wedding Retreat – Sleeps 20, 3 Kitchens, Nature Views
“The Hockley Hideaway”, sharing our unique property for your unique experiences❤️

“The Hockley Hideaway”, sharing our unique property for your unique experiences❤️

Mono ON
With a stay at this vacation home in Mono, you'll be next to a golf course, just a 4-minute walk from Hockley Valley Provincial Park and 10 minutes by foot from ...
Opens in a new window“The Hockley Hideaway”, sharing our unique property for your unique experiences❤️
Indoor Heated Pool• Outdoor Hot Tub • Sports Building• 15 acres Woodlands

Indoor Heated Pool• Outdoor Hot Tub • Sports Building• 15 acres Woodlands

Erin ON
With a stay at this vacation home in Erin, you'll be within a 15-minute drive of Hillsburgh Library and Forks of the Credit Provincial Park.
Opens in a new windowIndoor Heated Pool• Outdoor Hot Tub • Sports Building• 15 acres Woodlands
Elegant escape 4BR with POOL TABLE -Airport 20 min

Elegant escape 4BR with POOL TABLE -Airport 20 min

Brampton ON
When you stay at this vacation home in Brampton, you'll be within a 10-minute drive of Bowlero Brampton and Heart Lake Conservation Area.
Opens in a new windowElegant escape 4BR with POOL TABLE -Airport 20 min
Modern Spacious 4-bedroom house with WiFi, AC in Brampton

Modern Spacious 4-bedroom house with WiFi, AC in Brampton

Brampton ON
With a stay at this vacation home in Brampton, you'll be within a 5-minute drive of Heart Lake Conservation Area and Heart Lake.
Opens in a new windowModern Spacious 4-bedroom house with WiFi, AC in Brampton
Don't see what you're looking for?
See all available properties in Orangeville
View all properties
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.

Orangeville Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Orangeville vacation homes are the perfect way for you to wing it.

Holiday houses in Orangeville let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Orangeville in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Orangeville adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Orangeville with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Orangeville vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Orangeville Holiday Homes essential information

Accommodation
111 Holiday Homes
Lowest Price
AU$177
Highest Price
AU$215
Popular accommodation
Credit River Cottage, A rustic 4-season sanctuary in Inglewood, Caledon., Luxury 5-Bed Home w/ Office & 5 Baths | Peaceful Caledon Escape, Entire place, Ground level walkout Basement with Huge backyard, Cozy One bedroom suite 5min to Orangeville Downtown, Ravine Getaway | Family & Wedding Retreat – Sleeps 20, 3 Kitchens, Nature Views, “The Hockley Hideaway”, sharing our unique property for your unique experiences❤️, Indoor Heated Pool• Outdoor Hot Tub • Sports Building• 15 acres Woodlands, Elegant escape 4BR with POOL TABLE -Airport 20 min, Modern Spacious 4-bedroom house with WiFi, AC in Brampton

Top trending hotels in Orangeville

Best Western Plus Orangeville Inn & Suites

Best Western Plus Orangeville Inn & Suites

2.5 out of 5
7 Buena Vista Drive Orangeville ON
Fully refundableReserve now, pay when you stay
The price is AU$212 per night from 1 Apr to 2 Apr
AU$212
1 Apr - 2 Apr
includes taxes & fees
When you stay at Best Western Plus Orangeville Inn & Suites in Orangeville, you'll be near ski lifts, within a 5-minute drive of Island Lake Conservation Area ...
Opens in a new windowBest Western Plus Orangeville Inn & Suites
Atlanta Motel

Atlanta Motel

2 out of 5
316 Broadway Ave Orangeville ON
Located in Orangeville, Atlanta Motel is within a 5-minute drive of Theatre Orangeville and Island Lake Conservation Area.
Opens in a new windowAtlanta Motel
Entire place, Ground level walkout Basement  with Huge backyard

Entire place, Ground level walkout Basement with Huge backyard

Orangeville ON
The price is AU$177 per night from 31 Mar to 1 Apr
AU$177
31 Mar - 1 Apr
includes taxes & fees
Located in Orangeville, this vacation home is a 4-minute drive from Theatre Orangeville and 6 minutes from Island Lake Conservation Area.
Opens in a new windowEntire place, Ground level walkout Basement with Huge backyard
Save an average of 15% on thousands of hotels when you're signed in
Cozy One bedroom suite 5min to Orangeville Downtown

Cozy One bedroom suite 5min to Orangeville Downtown

Orangeville ON
The price is AU$215 per night from 31 Mar to 1 Apr
AU$215
31 Mar - 1 Apr
includes taxes & fees
A stay at this vacation home places you in the heart of Orangeville, within a 5-minute drive of Island Lake Conservation Area and Theatre Orangeville.
Opens in a new windowCozy One bedroom suite 5min to Orangeville Downtown
Don't see what you're looking for?
See all available properties in Orangeville
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.