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Top Holiday Rentals in Orangeville

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 £92
includes taxes & fees
4 Sept - 5 Sept
Entire place, Ground level walkout Basement with Huge backyard

Newly Reno’d Basement Suite w/ Private Access—10 min walk to Headwaters Hospital

9.0 out of 10, Wonderful, (6)
"Orangeville is a great town, this property is located SE side of town near the hospital but great easy access to town. Property Manager was very easy to get a hold of no major issues for our stay. I do suggest bringing paper towels or napkins was not able to locate on the property."
The price is £250
includes taxes & fees
29 Aug - 30 Aug
Newly Reno’d Basement Suite w/ Private Access—10 min walk to Headwaters Hospital

The Perfect Getaway

The price is £150
includes taxes & fees
1 Sept - 2 Sept
The Perfect Getaway

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 £248
includes taxes & fees
1 Sept - 2 Sept
Spotless Bright Home By The Headwaters In Orangeville!

Walk to Downtown or conservation area, 2 Bedroom home . Sleeps 4. Pets welcomed

10.0 out of 10, Exceptional, (9)
"Very nice house, easily walkable to grocery etc."
Walk to Downtown or conservation area, 2 Bedroom home . Sleeps 4. Pets welcomed

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

10.0 out of 10, Exceptional, (16)
"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

Gorgeous cozy cottage besides a bustling stream, surrounded by gorgeous greenery

8.4 out of 10, Very good, (12)
"This is such a beautiful little house, it really feels like your deep in the woods but in reality you're down the street from grocery stores! Would absolutely book again, and hope to in the future!"
Gorgeous cozy cottage besides a bustling stream, surrounded by gorgeous greenery

Belwood Bunkie Escape & Spa minutes away from Elora

10.0 out of 10, Exceptional, (4)
"A lovely and unique property, felt very special and comfy"
The price is £132
includes taxes & fees
7 Sept - 8 Sept
Belwood Bunkie Escape & Spa minutes away from Elora

Glamping by Lavender Farm, Brewery, Mono Cliffs, Hockley Valley

10.0 out of 10, Exceptional, (7)
"This place is amazing would highly recommend "
The price is £170
includes taxes & fees
1 Sept - 2 Sept
Glamping by Lavender Farm, Brewery, Mono Cliffs, Hockley Valley

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

10.0 out of 10, Exceptional, (2)
"We enjoyed our stay. The house was unique with lots of space. The surrounding area was beautiful. "
The price is £497
includes taxes & fees
8 Sept - 9 Sept
Hills and Valleys of Silver Creek – A Timeless 5 Bedroom Century Home Retreat.

Beautiful Bungalow on Grand River in Fergus.

9.6 out of 10, Exceptional, (10)
"Beautiful view of the river and wonderful hosts."
The price is £220
includes taxes & fees
7 Sept - 8 Sept
Beautiful Bungalow on Grand River in Fergus.

Tamarack Trails - Wilderness Cabin

Tamarack Trails - Wilderness Cabin

Luxury Chic 2BED End Unit in Central Brampton

2.0 out of 10, (1)
"This unit was not as advertised - nowhere near luxury or chic. Photo was deceiving as unit was way underground and was old and tired. I ended up not staying there at all and forfeited the money I paid! "
The price is £103
includes taxes & fees
2 Sept - 3 Sept
Luxury Chic 2BED End Unit in Central Brampton

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

The price is £676
includes taxes & fees
15 Sept - 16 Sept
6-bedroom house in enchanting Caledon Village with WiFi, AC, fitness equipment

Lakeview resort style suite (Twin or King)

9.2 out of 10, Wonderful, (5)
"Very friendly host. Quiet, peaceful surroundings. Nice galley kitchen. Enjoyed the lake access for sitting around and for fishing. "
The price is £103
includes taxes & fees
7 Sept - 8 Sept
Lakeview resort style suite (Twin or King)

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

8.0 out of 10, Very good, (1)
"Great location! House was very clean on the main level but unfinished in the basement. Wifi was not great but likely due to location more than anything. A couple of issues arose during stay however communication with property management /owner was excellent and issues were rectified right away. "
Charming 4-bedroom house in Caledon East with WiFi, AC

Your Luxurious Caledon escape close to everywhere

The price is £142
includes taxes & fees
3 Sept - 4 Sept
Your Luxurious Caledon escape close to everywhere

Fastbear 2

The price is £269
includes taxes & fees
29 Aug - 30 Aug
Fastbear 2

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

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

Quiet Forest Cabin

9.4 out of 10, Exceptional, (3)
"Quiet and cozy cabin. Host prepared loads of stuffs for us to enjoy a gathering time. Really nice place for us! "
The price is £106
includes taxes & fees
29 Aug - 30 Aug
Quiet Forest Cabin
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

Find out more about Orangeville

Find out more about Orangeville

Everything you need to know about Orangeville holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Orangeville holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Orangeville holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Orangeville holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Orangeville. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Orangeville holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Orangeville holiday rentals we have selected for you start as low as £92 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Orangeville rentals

At Expedia, we put the best Orangeville holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Orangeville rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Orangeville holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Orangeville. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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. Some other homes for rent in Orangeville include The Perfect Getaway and Spotless Bright Home By The Headwaters In Orangeville!.

How many holiday rentals are there in Orangeville?

Expedia has 9 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. Hockley Valley Resort and Osprey Valley Golf 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.