Book Holiday Homes in Orangeville

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Featured Holiday Homes in Orangeville

Fall Nordic Cottage Retreat with Hot Tub 60 Minutes from City

Fall Nordic Cottage Retreat with Hot Tub 60 Minutes from City

Caledon ON
Enjoy laundry facilities, in-room fireplaces and air conditioning. Popular attractions Heathlands Links at Osprey Valley and Forks of the Credit Provincial Park ...
Opens in a new windowFall Nordic Cottage Retreat with Hot Tub 60 Minutes from City
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 out of 5
Brampton ON
The price is NZ$1,106 per night from 24 Dec to 25 Dec
NZ$1,106
24 Dec - 25 Dec
includes taxes & fees
Stay at this holiday home in Brampton. Enjoy laundry facilities and air conditioning. Popular attractions The Old Pro Driving Range and Georgetown Market Place ...
Opens in a new windowVRBO 6 Queen Beds in 6 Bedrooms with 3 Bedrooms Having Attached Bath
Bright Private Coach House | Above Ground

Bright Private Coach House | Above Ground

Brampton ON
Stay at this holiday home in Brampton. Enjoy laundry facilities, an in-room coffee maker and air conditioning. Popular attractions Professor's Lake Recreation ...
Opens in a new windowBright Private Coach House | Above Ground
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The Perfect Getaway

The Perfect Getaway

Orangeville ON
The price is NZ$267 per night from 7 Jan to 8 Jan
NZ$267
7 Jan - 8 Jan 2026
includes taxes & fees
Stay at this holiday home in Orangeville. Enjoy laundry facilities, in-room fireplaces and air conditioning. Popular attractions Theatre Orangeville and Island ...
Opens in a new windowThe Perfect Getaway
Fastbear 2

Fastbear 2

Brampton ON
The price is NZ$615 per night from 2 Jan to 3 Jan
NZ$615
2 Jan - 3 Jan 2026
includes taxes & fees
Stay at this holiday home in Brampton. Enjoy laundry facilities and air conditioning. Popular attractions Professor's Lake Recreation Centre and Bowlero Brampton ...
Opens in a new windowFastbear 2
5BR Riverfront Retreat w/ Firetable, BBQ, and Deck

5BR Riverfront Retreat w/ Firetable, BBQ, and Deck

Orangeville ON
Stay at this holiday home in Mono. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Hockley Valley Resort and Hockley Valley Provincial ...
Opens in a new window5BR Riverfront Retreat w/ Firetable, BBQ, and Deck
Luxury Comfort and Convenience

Luxury Comfort and Convenience

3 out of 5
72 Donald Stewart Rd Brampton ON
Stay at this holiday home in Brampton. Enjoy free Wi-Fi and free parking. Popular attractions The Old Pro Driving Range and Great War Flying Museum are located ...
Opens in a new windowLuxury Comfort and Convenience
Beautiful Bungalow on Grand River in Fergus.

Beautiful Bungalow on Grand River in Fergus.

Fergus ON
The price is NZ$503 per night from 24 Dec to 25 Dec
NZ$503
24 Dec - 25 Dec
includes taxes & fees
Stay at this holiday home in Centre Wellington. Enjoy free Wi-Fi, a garden and patios. Popular attractions Belwood Lake Conservation Area and Elora Quarry Conservation ...
Opens in a new windowBeautiful Bungalow on Grand River in Fergus.
6-bedroom house in enchanting Caledon Village with WiFi, AC, fitness equipment

6-bedroom house in enchanting Caledon Village with WiFi, AC, fitness equipment

Caledon Village ON
The price is NZ$1,547 per night from 2 Jan to 3 Jan
NZ$1,547
2 Jan - 3 Jan 2026
includes taxes & fees
Stay at this holiday home in Caledon. Enjoy a fitness centre, laundry facilities and air conditioning. Popular attractions Caledon Country Club and Cheltenham ...
Opens in a new window6-bedroom house in enchanting Caledon Village with WiFi, AC, fitness equipment
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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
NZ$156
Highest Price
NZ$1,547
Popular accommodation
Fall Nordic Cottage Retreat with Hot Tub 60 Minutes from City, VRBO 6 Queen Beds in 6 Bedrooms with 3 Bedrooms Having Attached Bath, Bright Private Coach House | Above Ground, The Perfect Getaway, Fastbear 2, 5BR Riverfront Retreat w/ Firetable, BBQ, and Deck, Luxury Comfort and Convenience, Beautiful Bungalow on Grand River in Fergus., 6-bedroom house in enchanting Caledon Village with WiFi, AC, fitness equipment

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
The price is NZ$267 per night from 24 Dec to 25 Dec
NZ$267
24 Dec - 25 Dec
includes taxes & fees
Stay at this business-friendly hotel in Orangeville. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. ...
Opens in a new windowBest Western Plus Orangeville Inn & Suites
Atlanta Motel

Atlanta Motel

2 out of 5
316 Broadway Ave Orangeville ON
Fully refundableReserve now, pay when you stay
The price is NZ$156 per night from 29 Dec to 30 Dec
NZ$156
29 Dec - 30 Dec
includes taxes & fees
Stay at this motel in Orangeville. Enjoy free Wi-Fi, a 24-hour front desk and daily housekeeping. Popular attractions Theatre Orangeville and Island Lake Conservation ...
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 NZ$209 per night from 24 Dec to 25 Dec
NZ$209
24 Dec - 25 Dec
includes taxes & fees
Stay at this holiday home in Orangeville. Enjoy cable/satellite TV service and air conditioning. Popular attractions Theatre Orangeville and Island Lake Conservation ...
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
The Perfect Getaway

The Perfect Getaway

Orangeville ON
The price is NZ$267 per night from 7 Jan to 8 Jan
NZ$267
7 Jan - 8 Jan 2026
includes taxes & fees
Stay at this holiday home in Orangeville. Enjoy laundry facilities, in-room fireplaces and air conditioning. Popular attractions Theatre Orangeville and Island ...
Opens in a new windowThe Perfect Getaway
Don't see what you're looking for?
See all available properties in Orangeville
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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.