Orangeville Holiday Rentals

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Holiday Rentals in Orangeville

Cabin in Lena

10.0 out of 10, Exceptional, (11)
"Quiet, clean and absolutely lovely cabin! "
United States
Holley B.
The price is NZ$300
includes taxes & fees
30 Nov - 1 Dec
Peace & Simplicity in a Little Red Cabin on the Farm

Holiday Home in 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 NZ$464
includes taxes & fees
23 Nov - 24 Nov
MJ's Penthouse ,a piece of paradise on Monroe's historic square

Holiday Home in 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

Holiday Home in 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

Holiday Home in 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 NZ$510
includes taxes & fees
3 Dec - 4 Dec
Beautiful two story, downtown home, one block from the Square,

Holiday Home in 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

Holiday Home in Darlington

2.0 star property
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

Holiday Home in Darlington

9.2 out of 10, Wonderful, (31)
"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

Apartment in 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!

Cabin in 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 NZ$1,196
includes taxes & fees
24 Nov - 25 Nov
Avail. Christmas! Lake Cabin w/King, Sauna

Holiday Home in 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!

Cottage in Monroe

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

Holiday Home in 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

Cabin in Pearl City

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!"
United States
Andrew R.
The price is NZ$576
includes taxes & fees
17 Dec - 18 Dec
The Rustic Retreat: Elegant cabin with WiFi & AC in an enchanting location!

Holiday Home in Lena

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

Holiday Home in Monroe

7 blocks from downtown cheese days!

Holiday Home in Darlington

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

Apartment in Monroe

2.0 star property
The price is NZ$412
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 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 NZ$300 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.

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

MJ's Penthouse ,a piece of paradise on Monroe's historic square: This holiday home rental outside of Orangeville is located in the city centre, and has a balcony, a selection of games and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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 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.