Search Vacation Homes in Orangeville

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

Compare 92 Vacation Homes in Orangeville with updated reviews, rates, and availability.

Hockley “Hidden Treasure” a magical getaway!
Outdoor pool, a heated pool

Hockley “Hidden Treasure” a magical getaway!

10.0 out of 10, Exceptional, (30)
"We really enjoyed the house, pool and hot tub. There was lots of space and the house has a great cottage feel. Will definitely be back."
Hockley “Hidden Treasure” a magical getaway!
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

8.0 out of 10, Very Good, (6)
"The property was fantastic to stay at. We had a beautiful fire, lots of open space Frank was a pleasure to deal with the house was nice and big.Everything was provided for us that we needed"
House with 4.5 bedrooms,10 Acres of forest creek and trails, lots of parking
Serenity in the Hills - Charming 1-bdrm house w WiFi and Hot Tub in Orangeville
Smart TV, fireplace, video games, books

Serenity in the Hills - Charming 1-bdrm house w WiFi and Hot Tub in Orangeville

10.0 out of 10, Exceptional, (1)
"Very clean, modern, well equipped kitchen, gas fireplace and functioning hot tub"
The price is AED 319
AED 594 total
includes taxes & fees
1 May - 2 May
Serenity in the Hills - Charming 1-bdrm house w WiFi and Hot Tub in Orangeville
Beautiful New Build by Elora
Interior

Beautiful New Build by Elora

The price is AED 396
AED 913 total
includes taxes & fees
6 May - 7 May
Beautiful New Build by Elora
Charming Erin Country House near downtown
Private kitchen

Charming Erin Country House near downtown

The price is AED 797
AED 1,335 total
includes taxes & fees
1 May - 2 May
Charming Erin Country House near downtown
Entire place, Ground level walkout Basement with Huge backyard
2 bedrooms, WiFi, bed sheets

Entire place, Ground level walkout Basement with Huge backyard

7.2 out of 10, Good, (17)
"It was just fine for a nights stay. Owners were freindly and helpful"
The price is AED 183
AED 435 total
includes taxes & fees
1 May - 2 May
Entire place, Ground level walkout Basement with Huge backyard
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
Cozy Modern Retreat Minutes from Pearson Airport – Perfect for Travelers!
Exterior

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

10.0 out of 10, Exceptional, (1)
"We had a nice and calm stay.Rajan made sure we had everything we needed. He allowed us to use the laundry. Gave us sugar packet for chai. And offered bringing grocery as well.I definitely consider staying here again."
Cozy Modern Retreat Minutes from Pearson Airport – Perfect for Travelers!
Fastbear 2
Exterior

Fastbear 2

The price is AED 425
AED 687 total
includes taxes & fees
5 May - 6 May
Fastbear 2
Elegant and Modern Bolton Stay
Interior

Elegant and Modern Bolton Stay

Elegant and Modern Bolton Stay
*Luxury Retreat* 100-Acre Estate With Indoor Pool in East Garafax Ontario!
Property grounds

*Luxury Retreat* 100-Acre Estate With Indoor Pool in East Garafax Ontario!

2.0 out of 10, (1)
"NO ONE should book with this person - he cancelled on me and my family of 35 people LESS than an hour before our stay because he said he has just found out a few minutes before out check in that the heat in the house was not working. Then he was trying to take our money and offer us a much smaller less appealing looking place for 35 people which would have been impossible to fit anyways. And its been over a weeks time and i have still NOT received my refund. Do NOT make the same mistake I did,...
The price is AED 4,249
AED 8,018 total
includes taxes & fees
2 May - 3 May
*Luxury Retreat* 100-Acre Estate With Indoor Pool in East Garafax Ontario!
Amazing Fun Place With 6 Beds 3.5 Bath Home Having 14 People Sleeping Capacity
Exterior

Amazing Fun Place With 6 Beds 3.5 Bath Home Having 14 People Sleeping Capacity

10.0 out of 10, Exceptional, (1)
The price is AED 1,325
AED 2,740 total
includes taxes & fees
5 May - 6 May
Amazing Fun Place With 6 Beds 3.5 Bath Home Having 14 People Sleeping Capacity
Private Estate Home In Caledon Ontario! *6 Acres*
TV

Private Estate Home In Caledon Ontario! *6 Acres*

10.0 out of 10, Exceptional, (1)
The price is AED 1,854
AED 3,250 total
includes taxes & fees
1 May - 2 May
Private Estate Home In Caledon Ontario! *6 Acres*
The Halton Estate - Perfect For Family Gatherings
Interior

The Halton Estate - Perfect For Family Gatherings

The price is AED 2,390
AED 4,114 total
includes taxes & fees
5 May - 6 May
The Halton Estate - Perfect For Family Gatherings
Spotless & Clean 4 Bed 2.5 Bath Home , Upstair By The Headwaters In Orangeville!
Smart TV

Spotless & Clean 4 Bed 2.5 Bath Home , Upstair By The Headwaters In Orangeville!

9.0 out of 10, Wonderful, (4)
"The house was exactly as advertised, clean, very central to Orangeville, and checking in was a breeze. I would be more than happy to stay there again if the opportunity arises. The hostess was also very helpful and responsive."
The price is AED 571
AED 1,251 total
includes taxes & fees
2 May - 3 May
Spotless & Clean 4 Bed 2.5 Bath Home , Upstair By The Headwaters In Orangeville!
Luxury Comfort and Convenience
Family House | Living area

Luxury Comfort and Convenience

3.0 star property
The price is AED 507
AED 1,392 total
includes taxes & fees
28 May - 29 May
Luxury Comfort and Convenience
Luxury Retreat with Workspace & Spacious Backyard
Fridge, microwave, oven, stovetop

Luxury Retreat with Workspace & Spacious Backyard

10.0 out of 10, Exceptional, (2)
"So convenient for any age host was very nice to reply back I would recommend other people "
Luxury Retreat with Workspace & Spacious Backyard
Beautiful & Private Mid Century Modern House on 10 Acres near Caledon!
Smart TV, fireplace, video games, books

Beautiful & Private Mid Century Modern House on 10 Acres near Caledon!

10.0 out of 10, Exceptional, (32)
"This is our second summer staying at Howie's. It is a lovely property and one of a kind space. Howie is always responsive and friendly. Highly recommend for a family retreat in the country."
Beautiful & Private Mid Century Modern House on 10 Acres near Caledon!
Fields & Sunsets
Interior

Fields & Sunsets

10.0 out of 10, Exceptional, (1)
"My family and I stayed over the Christmas Holiday for 4 nights. We hosted a family gathering for Christmas dinner for 17 people and the property was perfect for the event! The host was kind enough to put up a Christmas tree and do some light decorations around the main floor as well. The property is wonderfully updated and comfortable. Master bedroom suite is gorgeous! Easy communication with the host. Would definitely stay at this property again!"
Fields & Sunsets
Century home 3 bed with Gas Fireplace/fenced yard and 5 minute walk to Broadway
Exterior

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

10.0 out of 10, Exceptional, (14)
"We had a great stay here, clean, comfortable beds and an attentive host! "
Century home 3 bed with Gas Fireplace/fenced yard and 5 minute walk to Broadway
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.
Don't see what you're looking for?
See all available properties in Orangeville
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Orangeville

Serenity in the Hills - Charming 1-bdrm house w WiFi and Hot Tub in Orangeville
Smart TV, fireplace, video games, books

Serenity in the Hills - Charming 1-bdrm house w WiFi and Hot Tub in Orangeville

10.0 out of 10, Exceptional, (1)
"Very clean, modern, well equipped kitchen, gas fireplace and functioning hot tub"
The price is AED 319
AED 594 total
includes taxes & fees
1 May - 2 May
Serenity in the Hills - Charming 1-bdrm house w WiFi and Hot Tub in Orangeville
Spotless & Clean 4 Bed 2.5 Bath Home , Upstair By The Headwaters In Orangeville!
Smart TV

Spotless & Clean 4 Bed 2.5 Bath Home , Upstair By The Headwaters In Orangeville!

9.0 out of 10, Wonderful, (4)
"The house was exactly as advertised, clean, very central to Orangeville, and checking in was a breeze. I would be more than happy to stay there again if the opportunity arises. The hostess was also very helpful and responsive."
The price is AED 571
AED 1,251 total
includes taxes & fees
2 May - 3 May
Spotless & Clean 4 Bed 2.5 Bath Home , Upstair By The Headwaters In Orangeville!
Entire place, Ground level walkout Basement with Huge backyard
2 bedrooms, WiFi, bed sheets

Entire place, Ground level walkout Basement with Huge backyard

7.2 out of 10, Good, (17)
"It was just fine for a nights stay. Owners were freindly and helpful"
The price is AED 183
AED 435 total
includes taxes & fees
1 May - 2 May
Entire place, Ground level walkout Basement with Huge backyard
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.