A cityscape with a mix of historic and modern buildings, a parking lot, and a river in the background.

Orangeville Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Orangeville vacation rentals

A modern kitchen with white cabinets, a wooden island, stainless steel appliances, and a bar stool.

1. Cozy Basement Apartment (700 sq ft) with Full Kitchen

Cozy Basement Apartment (700 sq ft) with Full Kitchen
Orangeville
9.0 out of 10, Wonderful, (2 reviews)
"Great location!"
Canada
Kefa
$94 nightly
The price is $107
Nov 14 - Nov 15
Total with taxes and fees
Cozy Basement Apartment (700 sq ft) with Full Kitchen
A modern kitchen with a built-in oven, microwave, and stove. There is a dining area with a round table and two chairs. A black sofa and a small side table are in the living area.

2. The Perfect Getaway

The Perfect Getaway
Orangeville
7.8 out of 10, Good, (10 reviews)
"Happy with everything, but we couldn't get any channels on the SmartTV."
Canada
Andrea
$185 nightly
The price is $209
Nov 14 - Nov 15
Total with taxes and fees
The Perfect Getaway
A two-story brick house with a patio area.

3. Entire place, Ground level walkout Basement with Huge backyard

Entire place, Ground level walkout Basement with Huge backyard
Orangeville
7.4 out of 10, Good, (40 reviews)
"Loved our accommodations! Exactly what we were looking for! Will book next year! Thank you!"
Canada
Darlene M
$102 nightly
The price is $115
Dec 6 - Dec 7
Total with taxes and fees
Entire place, Ground level walkout Basement with Huge backyard
A deck with two white lounge chairs and a red railing overlooking a lake.

4. Lakeside Private suite (Queen bed room)

Lakeside Private suite (Queen bed room)
Loretto
8.0 out of 10, Very good, (4 reviews)
"We really enjoyed our stay, the place was clean and comfortable. Thank you so much."
Canada
Michael W.
$97 nightly
The price is $109
Nov 15 - Nov 16
Total with taxes and fees
Lakeside Private suite (Queen bed room)
A room with wooden walls and a bed with a nature-themed duvet.

5. Bright and Cozy Tiny Pine House

Bright and Cozy Tiny Pine House
Erin
8.0 out of 10, Very good, (1 review)
$90 nightly
The price is $101
Nov 12 - Nov 13
Total with taxes and fees
Bright and Cozy Tiny Pine House
A wooden deck with chairs and tables overlooking a lake, a flag, and a gazebo.

6. Lakeview private suite with kitchen (Twin or King)

Lakeview private suite with kitchen (Twin or King)
Loretto
8.6 out of 10, Excellent, (8 reviews)
"Beautiful spot to stay! Highly recommended "
United States
Patrick S.
$118 nightly
The price is $133
Nov 15 - Nov 16
Total with taxes and fees
Lakeview private suite with kitchen (Twin or King)
A backyard with a patio, a small shed, and a wooden fence.

7. Studio Apartment in the heart of Caledon

Studio Apartment in the heart of Caledon
CALEDON EAST
8.8 out of 10, Excellent, (8 reviews)
"Beautiful flat !"
Canada
Jaivyn
$68 nightly
The price is $77
Nov 17 - Nov 18
Total with taxes and fees
Studio Apartment in the heart of Caledon
A wooden deck with chairs and tables overlooking a lake, a flag, and a gazebo.

8. Resort style entire guesthouse with kitchen (2 rooms)

Resort style entire guesthouse with kitchen (2 rooms)
Loretto
5.4 out of 10, (3 reviews)
"Very easy check in "
Canada
Carly C.
$152 nightly
The price is $171
Nov 12 - Nov 13
Total with taxes and fees
Resort style entire guesthouse with kitchen (2 rooms)
A modern kitchen with white cabinets, stainless steel appliances, and a dining area with a wooden table and chairs.

9. Charming Erin Country House near downtown

Charming Erin Country House near downtown
Erin
7.4 out of 10, Good, (15 reviews)
"Wonderful place. Check in was super easy. Upon entering, everything was very clean with towels and other essentials laid out. House was very beautiful and cozy. "
Canada
Joshveer S.
$228 nightly
The price is $257
Nov 18 - Nov 19
Total with taxes and fees
Charming Erin Country House near downtown
An aerial view of a riverside property with a large building, a garden, and a small pond.

10. Beautiful Bungalow on Grand River in Fergus.

Beautiful Bungalow on Grand River in Fergus.
Fergus
9.8 out of 10, Exceptional, (30 reviews)
"Great place!"
Canada
Lariska
$238 nightly
The price is $268
Nov 19 - Nov 20
Total with taxes and fees
Beautiful Bungalow on Grand River in Fergus.
Outdoor dining

11. Peaceful Forest Retreat with Fire Pit and BBQ Near Mansfield Ski Club

Peaceful Forest Retreat with Fire Pit and BBQ Near Mansfield Ski Club
Mulmur
2.0 out of 10, (1 review)
"They double booked and didn’t mention anything till I was able to reach out for check-in and didn’t help with making other plans for where to sleep or refund at all."
Canada
Quinn
$241 nightly
The price is $272
Nov 12 - Nov 13
Total with taxes and fees
Peaceful Forest Retreat with Fire Pit and BBQ Near Mansfield Ski Club
A residential building with a brick facade, a wooden deck, and a fenced backyard with outdoor seating.

12. Walkout Basement with Private Entrance

Walkout Basement with Private Entrance
Rosedale Village
10.0 out of 10, Exceptional, (6 reviews)
"We had a Great stay and felt very welcome. I would recommend this VRBO."
United States
mark h.
$228 nightly
The price is $257
Nov 18 - Nov 19
Total with taxes and fees
Walkout Basement with Private Entrance
A neatly made bed with a patterned blanket, a bedside lamp, and a nightstand with a drawer.

13. Modern 2BR Private Suite |Prime Location

Modern 2BR Private Suite |Prime Location
Mayfield West
2.0 out of 10, (1 review)
"The host was asking for more money for no reason"
Canada
Pavit
$171 nightly
The price is $194
Nov 12 - Nov 13
Total with taxes and fees
Modern 2BR Private Suite |Prime Location
A modern kitchen with a central island, bar stools, stainless steel appliances, and a fireplace.

14. Private Forest Getaway 4BR | Hot Tub & Pond

Private Forest Getaway 4BR | Hot Tub & Pond
Shelburne
$621 nightly
The price is $701
Nov 12 - Nov 13
Total with taxes and fees
Private Forest Getaway 4BR | Hot Tub & Pond
A modern kitchen with white cabinetry, a central island, and built-in appliances.

15. Caledon Estate

Caledon Estate
CALEDON
7.0 out of 10, Good, (2 reviews)
"Amenities were in extremely bad condition. Poor cleanliness than before. Often a go to spot for us. We invited our family and friends. They were not please with our communication and also on the experience."
United States
Rajesh B.
$687 nightly
The price is $777
Nov 12 - Nov 13
Total with taxes and fees
Caledon Estate
A wooden staircase with a handrail, leading to a landing with a chandelier.

16. Peaceful country home on 25 acres of wooded land

Peaceful country home on 25 acres of wooded land
Loretto
9.4 out of 10, Exceptional, (3 reviews)
"Check in was easy, the house was a good size to fit my party of 9. It would have been nice if some of the back yard grass was cut to play games and for my small dog. It would help to have a few more towels. The house was clean n comfortable."
Canada
Bev C.
$462 nightly
The price is $523
Nov 12 - Nov 13
Total with taxes and fees
Peaceful country home on 25 acres of wooded land
Interior

17. The Refresh Stream

The Refresh Stream
Sandalwood West
$804 nightly
The price is $908
Nov 16 - Nov 17
Total with taxes and fees
The Refresh Stream
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

Hampton Inn & Suites by Hilton Bolton

Hampton Inn & Suites by Hilton Bolton

10/10 Excellent
"I didn't use the pool or the fitness room so I can't comment on them. The suites however were modern and clean with fridge, microwave and coffee machine with packets. The free wifi if you are a points member or if you joined their page offered full streaming capabilities with instructions. Breakfast consisted of a cheese or western omelet with sausage, potatoes and toast as well as waffles, fruit, muffins, cereal and yogurt. There was complementary tea and coffee available all day as well. There was no onsite dining but there's an A&W in the parking lot as well as several restaurants close by and a Walmart across the street I would definitely stay there again."
Gaye Laing 2-night trip
Posted 22 hours ago
Hampton Inn & Suites by Hilton Bolton

Find out more about Orangeville

Everything you need to know about Orangeville vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Orangeville vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Orangeville vacation 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 low season months. For more hustle and bustle, you may prefer to visit Orangeville in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $101 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Orangeville rentals

At Expedia, we put the best Orangeville vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Orangeville?

Yes, we give you a choice of vacation rentals close to the most popular attractions in Orangeville, or you can choose a more secluded option if you want a relaxing place to 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 vacation rentals in Orangeville?

Walk to Downtown or conservation area, 2 Bedroom home . Sleeps 4. Pets welcomed: Visitors like this Orangeville vacation home rental. It is located near skiing and has a balcony, a garden, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Orangeville?

Expedia has 12 vacation 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. Orangeville Farmers' Market and Alton Mill Arts Centre are a couple of places you'll find in the larger area.

What’s a vacation rental in Orangeville like?

Vacation rentals are privately owned properties you can stay in for a few weeks or just a few days in Orangeville. Vacation rentals offer amenities like kitchens and laundry facilities so you'll have a home away from home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for a family getaway.