Holiday Homes in Orangeville

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Holiday Homes in Orangeville and around

The Caledon Retreat
Outdoor pool

The Caledon Retreat

10.0 out of 10, Exceptional, (2)
"amazing stay , great communication, beautiful house , had many assets to make your stay comfortable will definitely be coming back !"
The price is €577
includes taxes & fees
17 Aug - 18 Aug
The Caledon Retreat
Entire place, Ground level walkout Basement with Huge backyard
2 bedrooms, WiFi, bed sheets

Entire place, Ground level walkout Basement with Huge backyard

7.0 out of 10, Good, (21)
"It was an odd setup but worked for our needs"
The price is €107
includes taxes & fees
15 Aug - 16 Aug
Entire place, Ground level walkout Basement with Huge backyard
Beautiful Bungalow on Grand River in Fergus.
Exterior

Beautiful Bungalow on Grand River in Fergus.

9.8 out of 10, Exceptional, (9)
"Beautiful view of the river and wonderful hosts."
The price is €214
includes taxes & fees
18 Aug - 19 Aug
Beautiful Bungalow on Grand River in Fergus.
Hills and Valleys of Silver Creek – A Timeless 5 Bedroom Century Home Retreat.
Exterior

Hills and Valleys of Silver Creek – A Timeless 5 Bedroom Century Home Retreat.

10.0 out of 10, Exceptional, (1)
"We enjoyed our stay. The house was unique with lots of space. The surrounding area was beautiful. "
Hills and Valleys of Silver Creek – A Timeless 5 Bedroom Century Home Retreat.
The Perfect Getaway
Microwave, oven, stovetop

The Perfect Getaway

The price is €173
includes taxes & fees
15 Aug - 16 Aug
The Perfect Getaway
5-Bedroom Countryside Estate in Northern GTA – Ideal for Gatherings & Getaways
Microwave, oven, stovetop, dishwasher

5-Bedroom Countryside Estate in Northern GTA – Ideal for Gatherings & Getaways

10.0 out of 10, Exceptional, (1)
"House was very nice, lots of space. Stay was very nice, Jagjit was a great host in being generous. I would book again and i suggest you book here. "
5-Bedroom Countryside Estate in Northern GTA – Ideal for Gatherings & Getaways
Charming 4-bedroom house in Caledon East with WiFi, AC
Living area

Charming 4-bedroom house in Caledon East with WiFi, AC

Charming 4-bedroom house in Caledon East with WiFi, AC
Luxury Comfort and Convenience
Family House | Living area

Luxury Comfort and Convenience

3.0 star property
2.0 out of 10, (1)
Luxury Comfort and Convenience
Bright Private Coach House | Above Ground
Exterior

Bright Private Coach House | Above Ground

10.0 out of 10, Exceptional, (1)
"It's so rare to find such a nice above ground apartment and at such a great price too. The apartment was beautiful, my family loved our stay and the host was wonderful and attentive."
Bright Private Coach House | Above Ground
House with 4.5 bedrooms,10 Acres of forest creek and trails, lots of parking
Interior

House with 4.5 bedrooms,10 Acres of forest creek and trails, lots of parking

8.4 out of 10, Very good, (13)
"Perfect location for family wedding in the area, home was clean and perfect size "
House with 4.5 bedrooms,10 Acres of forest creek and trails, lots of parking
Fastbear 2
Exterior

Fastbear 2

The price is €313
includes taxes & fees
26 Aug - 27 Aug
Fastbear 2
5BR Riverfront Retreat w/ Firetable, BBQ, and Deck
Terrace/patio

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

5BR Riverfront Retreat w/ Firetable, BBQ, and Deck
Redstone Retreat- Cozy countryhouse w/3 bedrooms
Private kitchen

Redstone Retreat- Cozy countryhouse w/3 bedrooms

Redstone Retreat- Cozy countryhouse w/3 bedrooms
“The Hockley Hideaway”, sharing our unique property for your unique experiences❤️
Outdoor pool, a heated pool

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

10.0 out of 10, Exceptional, (39)
"This property and location is the perfect place to stay as gorgeous inside as it is out. We and our two dogs were more than comfortable and hope to return again soon."
“The Hockley Hideaway”, sharing our unique property for your unique experiences❤️
Private Estate Home In Caledon Ontario! *6 Acres*
TV

Private Estate Home In Caledon Ontario! *6 Acres*

7.0 out of 10, Good, (2)
"Not anything like was advertised, outside looked like an abandoned house."
The price is €781
includes taxes & fees
27 Aug - 28 Aug
Private Estate Home In Caledon Ontario! *6 Acres*
Cozy Modern Retreat Minutes from Pearson Airport – Perfect for Travelers!
Exterior

Cozy Modern Retreat Minutes from Pearson Airport – Perfect for Travelers!

9.4 out of 10, Exceptional, (3)
"The property is in a great location, very clean with an excellent management team. They were there to make sure we had everything and enjoyed our stay. We will definitely rent this property for our next family trip."
Cozy Modern Retreat Minutes from Pearson Airport – Perfect for Travelers!
Spotless Bright Home By The Headwaters In Orangeville!
Smart TV

Spotless Bright Home By The Headwaters In Orangeville!

8.8 out of 10, Excellent, (5)
"We needed a place close to the Sonnen Hill Brewery for a family party and this was perfect. It was 5 minutes away. Amarjit was very responsive to questions prior to arrival and the check in process was perfect. The house was very clean and exactly as described."
The price is €289
includes taxes & fees
25 Aug - 26 Aug
Spotless Bright Home By The Headwaters In Orangeville!
Beautiful New Build by Elora
Interior

Beautiful New Build by Elora

10.0 out of 10, Exceptional, (5)
Beautiful New Build by Elora
Country Caledon Charm
Fireplace

Country Caledon Charm

10.0 out of 10, Exceptional, (1)
"We were looking for a quiet home to relax in between site seeing - and this house gave us everything we needed. It was quiet and away from the hustle and bustle of the big city but close enough for us to enjoy downtown Toronto, the zoo, Canada's Wonderland and more. Highly recommend."
Country Caledon Charm
Charming Erin Country House near downtown
Fridge, microwave, oven, stovetop

Charming Erin Country House near downtown

8.0 out of 10, Very good, (1)
"Three bedroom home with all amenities as described. Kitchen and bathrooms were clean and well equipped. Modern updated interior. Great for three couples. Thank you for having us!"
The price is €345
includes taxes & fees
18 Aug - 19 Aug
Charming Erin Country House near downtown
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Orangeville Hotel Reviews

Best Western Plus Orangeville Inn & Suites

Best Western Plus Orangeville Inn & Suites

10/10 Excellent
"Location was easy to find and accessible. Clean well laidout hotel and great rooms. Perfect location if visiting people at hospital. Layout of our room would make a great long stay location. A week to a month or so for students. With great kitchen set up. Just overall pleasant staff and"
Deborah Ann 1-night trip
Posted 2 days ago
Best Western Plus Orangeville Inn & Suites