Orangeville Holiday Rentals

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Holiday Rentals in Orangeville

Whispering Woods Estate - Relax, recharge, connect

10.0 out of 10, Exceptional, (1)
"This property exceeded our expectations. Communication with owners was perfect. Kitchen was well stocked with all our cooking needs. Bed very comfortable. Enjoyed the deck and grill. Large property for walking our dogs. We recommend this property and hope it is available the next time we are in the area. "
Whispering Woods Estate - Relax, recharge, connect

Peace & Simplicity in a Little Red Cabin on the Farm

10.0 out of 10, Exceptional, (8)
The price is AU$224
includes taxes & fees
8 Oct - 9 Oct
Peace & Simplicity in a Little Red Cabin on the Farm

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

10.0 out of 10, Exceptional, (18)
"We had a great time, nice and relaxing. Had everything we wanted."
The price is AU$485
includes taxes & fees
5 Oct - 6 Oct
Quite- relaxing country living with pool/hot tub and sauna!

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

10.0 out of 10, Exceptional, (154)
"Great location to roam around the southern area of Wisconsin"
3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe

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

10.0 out of 10, Exceptional, (34)
"Everything was very clean and welcoming. The decor was cute and cozy. Overall great stay."
The price is AU$442
includes taxes & fees
8 Oct - 9 Oct
Beautiful two story, downtown home, one block from the Square,

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

10.0 out of 10, Exceptional, (97)
"In town for girls getaway. This was our second stay at this location. Everything about the stay was perfect will definitely be back! Myron and Jane are great hosts. 10/10!!"
The price is AU$415
includes taxes & fees
20 Oct - 21 Oct
MJ's Penthouse ,a piece of paradise on Monroe's historic square

Historic Country Farmhouse for ANY Season!

10.0 out of 10, Exceptional, (45)
"Great weekend with girls. Host was very attentive. Location was great, close to shopping and wineries."
Historic Country Farmhouse for ANY Season!

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

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

KC HOUSE Cozy Country Home. Enjoy the country life!

10.0 out of 10, Exceptional, (16)
"More than we expected! We were so comfortable and loved every minute being there. We will definitely be back! "
KC HOUSE Cozy Country Home. Enjoy the country life!

Destination Driftless- A Trailside Retreat

9.4 out of 10, Exceptional, (30)
"Great place to stay. We werent at the house much. Just to sleep and get ready. House decor is very cute."
Destination Driftless- A Trailside Retreat

Avail. Octoberfest Sep 25th-28th-Lake Cabin w/King

10.0 out of 10, Exceptional, (4)
"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."
The price is AU$1,142
includes taxes & fees
15 Oct - 16 Oct
Avail. Octoberfest Sep 25th-28th-Lake Cabin w/King

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

2.5 star property
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!"
The Rustic Retreat: Elegant cabin with WiFi & AC in an enchanting location!

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

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

Apartment in private home, sleeps 7 guest

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

Wisconsin Farmhouse Stay: Utv, Boat, Snowmobile!

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

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

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

7 blocks from downtown cheese days!

7 blocks from downtown cheese days!

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

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

50 acre Private Reserve-Private Lake, Sugar River - Seclusion- Brodhead

50 acre Private Reserve-Private Lake, Sugar River - Seclusion- Brodhead

Lookout Loft over the Monroe Square

2.0 star property
The price is AU$351
includes taxes & fees
8 Oct - 9 Oct
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

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$224 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?

Whispering Woods Estate - Relax, recharge, connect: This holiday home rental outside of Orangeville is located in a rural location, and has a fireplace, a patio 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 stovetop and a microwave, so that you can cook with friends or family. Make the most of garden in this rental home to help you unwind.

What can I see and do in Orangeville?

Explore the area and family-friendly sights such as Sugar River Raceway, or get out into nature at a spot like Krape Park. 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.