Orangeville Holiday Rentals

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Holiday Rentals in Orangeville

Peace & Simplicity in a Little Red Cabin on the Farm

Lena
10.0 out of 10, Exceptional, (11)
"Quiet, clean and absolutely lovely cabin! "
United States
Holley B.
The price is AU$264
includes taxes & fees
2 Dec - 3 Dec
Peace & Simplicity in a Little Red Cabin on the Farm

MJ's Penthouse ,a piece of paradise on Monroe's historic square

Monroe
10.0 out of 10, Exceptional, (102)
"My husband and I stayed here and were so happy we did this home was beautiful and really something special. I highly recommend the stay here! "
United States
Katie B.
The price is AU$407
includes taxes & fees
20 Nov - 21 Nov
MJ's Penthouse ,a piece of paradise on Monroe's historic square

3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe

Monticello
10.0 out of 10, Exceptional, (156)
"A comfy home in a quiet location, perfect for our weekend getaway. We've stayed here once before and would definitely come back again if it's available next time we're in the area. "
United States
Amy K.
3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe

Whispering Woods Estate - Relax, recharge, connect

Rockton
8.8 out of 10, Excellent, (3)
"This was a phenomenal house, couldnt have been any better!"
United States
Cameron S.
Whispering Woods Estate - Relax, recharge, connect

Beautiful two story, downtown home, one block from the Square,

Monroe
10.0 out of 10, Exceptional, (35)
"Everything was very clean and welcoming. The decor was cute and cozy. Overall great stay."
United States
Jeff Z.
The price is AU$462
includes taxes & fees
2 Dec - 3 Dec
Beautiful two story, downtown home, one block from the Square,

Beautiful Log House 4 Bed, 2 Baths, 15 acre land, close to Madison, sleeps 13

Albany
9.6 out of 10, Exceptional, (4)
"This was a perfect place for our two night stay for four couples over Labor Day weekend. Very nice, well appointed interior and really comfortable beds! Would stay here again."
United States
Bob O.
Beautiful Log House 4 Bed, 2 Baths, 15 acre land, close to Madison, sleeps 13

Historic farmhouse with WiFi, dog-friendly, close to rec trails

2.0 star property
Darlington
9.8 out of 10, Exceptional, (11)
"its perfect place for spend good time from city "
United States
Anna W.
Historic farmhouse with WiFi, dog-friendly, close to rec trails

Destination Driftless- A Trailside Retreat

Darlington
9.4 out of 10, Exceptional, (30)
"We have stayed here a few times. Everything is a thumbs up. We will be booking again. Thanks for share your place with us."
United States
Christina R.
Destination Driftless- A Trailside Retreat

Quite- relaxing country living with pool/hot tub and sauna!

Pecatonica
10.0 out of 10, Exceptional, (18)
"Everything was as promised! Smooth and easy check in. Very clean and inviting. Outdoor amenities were in good shape, working and absolutely amazing! "
United States
Gail W.
Quite- relaxing country living with pool/hot tub and sauna!

Avail. Christmas! Lake Cabin w/King, Sauna

Brodhead
10.0 out of 10, Exceptional, (5)
"This is a beautiful home and area with a lot of fun activities. Love kayaking, playing pool, and sitting on the deck with the lake view."
United States
Jenelle K.
The price is AU$1,050
includes taxes & fees
24 Nov - 25 Nov
Avail. Christmas! Lake Cabin w/King, Sauna

KC HOUSE Cozy Country Home. Enjoy the country life!

Rock City
10.0 out of 10, Exceptional, (17)
"Beautifully maintained, stocked with any little thing you need. Clean, relaxing and suited our group perfectly for a weekend away. "
United States
Patricia M.
KC HOUSE Cozy Country Home. Enjoy the country life!

Wisconsin Farmhouse Stay: Utv, Boat, Snowmobile!

3.0 star property
Monroe
Wisconsin Farmhouse Stay: Utv, Boat, Snowmobile!

Apartment in private home, sleeps 7 guest

Freeport
10.0 out of 10, Exceptional, (6)
"Great experience! Hosts are great people. Would stay again if in the area. "
United States
Steve L.
Apartment in private home, sleeps 7 guest

The Rustic Retreat: Elegant cabin with WiFi & AC in an enchanting location!

2.5 star property
Pearl City
10.0 out of 10, Exceptional, (3)
"Out of half a dozen or so cabin rentals, this one is the absolute best. It's clean, uncluttered, quiet, and huge! Water was hot, heater worked really well (it was a very cold week) and the kitchen worked well. Beds were comfy too. I can't say enough good things about this place!"
United States
Andrew R.
The price is AU$502
includes taxes & fees
17 Dec - 18 Dec
The Rustic Retreat: Elegant cabin with WiFi & AC in an enchanting location!

Cozy 3 bedroom house off the Historical Stage Couch Trail in Lena Ill

Lena
Cozy 3 bedroom house off the Historical Stage Couch Trail in Lena Ill

7 blocks from downtown cheese days!

Monroe
7 blocks from downtown cheese days!

Charming 2-bedroom house with AC, WiFi in enchanting Darlington

2.0 star property
Darlington
Charming 2-bedroom house with AC, WiFi in enchanting Darlington

Lookout Loft over the Monroe Square

2.0 star property
Monroe
The price is AU$362
includes taxes & fees
8 Dec - 9 Dec
Lookout Loft over the Monroe Square
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

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, 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 favourite 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 depend 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 AU$264 per night. Entering your travel dates in the search wizard might find you 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.

What are some of the best holiday rentals that Orangeville has to offer?

3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe: This holiday home rental outside of Orangeville is located in a rural location, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

What can I see and do in Orangeville?

Explore the area and family-friendly sights such as SplashLand Family Water Park, or get out into nature at a spot like Jane Addams Recreation Trail. Historic Cheesemaking Center and Minhas Craft Brewery are a couple of places you'll find in the wider area.

What are holiday rentals like in Orangeville?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Orangeville. Holiday rentals feature amenities such as hot tubs, fire pits and patios so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of privacy away from public hotel lifts and lobbies packed with people while still allowing you to travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for a family trip or a small group gathering.