Orangeville Vacation Rentals

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Vacation Rentals in Orangeville

3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe
10.0 out of 10, Exceptional, 117 reviews
"The home was clean and quiet and very comfortable. We spent time on both the upstairs and downstairs porches drinking coffee in the morning, a little wine in the evenings. The only scary thing is the driveway up for me. No problem for my husband, though! Great place!! Would stay here again!"
3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe
Quite- relaxing country living with pool/hot tub and sauna!
10.0 out of 10, Exceptional, 15 reviews
"Like your own private resort on an affordable scale. Hot tub fantastic and setting idyllic."
The price is CA $274
CA $453 total
includes taxes & fees
Jun 19 - Jun 20
Quite- relaxing country living with pool/hot tub and sauna!
MJ's Penthouse ( a piece of paradise on Monroe's historic square)<br>
10.0 out of 10, Exceptional, 69 reviews
"It was beautiful and was a perfect location."
The price is CA $268
CA $359 total
includes taxes & fees
Jul 2 - Jul 3
MJ's Penthouse ( a piece of paradise on Monroe's historic square)<br>
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KC HOUSE Cozy Country Home
10.0 out of 10, Exceptional, 1 review
"Very peaceful! Very welcoming! This was a great place, blending old and new! Our group was 20 - 65 years old. All of the beds were comfy, the kitchen was well appointed. We really loved the outdoor cooking area and the outdoor seating areas. What a view! This would be a great place for a retreat and to unplug (although there is solid wifi and TVs throughout). The owner went over and above. We entered the house to an array of snacks and beverages on the counter. I can't say enough about this...
KC HOUSE Cozy Country Home
Historic Country Farmhouse for ANY Season!
10.0 out of 10, Exceptional, 34 reviews
"Great place to stay. The host was very helpful and accommodating. The house and property are kept up extremely nice. A lot of neat history all around. I look forward to staying again."
Historic Country Farmhouse for ANY Season!
Destination Driftless- A Trailside Retreat
9.4 out of 10, Exceptional, 21 reviews
"Wondering location not far from the ATV trails loved the old farm house feel and decor will definitely stay again hopefully longer next time !!"
Destination Driftless- A Trailside Retreat
Beautiful downtown home, one block from the Square,
10.0 out of 10, Exceptional, 19 reviews
"This house was so cute! Modern decor and amenities with beautifully restored original hardwood floors. We would definitely stay here again! 😁"
The price is CA $291
CA $492 total
includes taxes & fees
Jun 25 - Jun 26
Beautiful downtown home, one block from the Square,
Waterfront Sugar River Cabin w/ Dock & Game Room!
9.0 out of 10, Wonderful, 2 reviews
"I stayed here with a few friends on a Reading Retreat. The house was beautiful and the location quiet and secluded. We loved that the kitchen and space was well stocked and had everything we needed."
Waterfront Sugar River Cabin w/ Dock & Game Room!
Entire lower level in a private home with walkout fenced yard.
9.2 out of 10, Wonderful, 7 reviews
"This was the perfect place to stay in Freeport! It was beautiful and was so clean that it felt like we were the first to stay there. It had everything we needed and SO much room, which was great as we were staying with a toddler. There is a family living above, which you could occasionally hear during the day, but it didn’t bother us at all! We would stay here again in a heartbeat and likely will next time we visit family!"
Entire lower level in a private home with walkout fenced yard.
Apartment in private home, sleeps 7 guest
10.0 out of 10, Exceptional, 3 reviews
"Warm and spacious. Great hosts. We had a party of 5 and were very comfortable. There is a warm feel to the decor and everything was top notch!"
Apartment in private home, sleeps 7 guest
Spacious Villa*Beautiful Views*Country Setting
10.0 out of 10, Exceptional, 7 reviews
"We use VRBO in place of extended stay hotels for work. We look at clean,quiet places. This home is that!! The owners were very responsive the one time we needed them. The house has tons of room, great for large groups. Close to town yet not too close. Will use again."
Spacious Villa*Beautiful Views*Country Setting
Cozy Countryside Getaway @ Kerlin Schoolhouse
Cozy Countryside Getaway @ Kerlin Schoolhouse
Waterfront Sugar River Cabin w/ Dock & Game Room!
3.0 star property
Waterfront Sugar River Cabin w/ Dock & Game Room!
7 blocks from downtown cheese days!
7 blocks from downtown cheese days!
Getaway to the country to enjoy the outdoors and sunset country views.
The price is CA $240
CA $327 total
includes taxes & fees
Jul 17 - Jul 18
Getaway to the country to enjoy the outdoors and sunset country views.
Wisconsin Farmhouse Stay: Utv, Boat, Snowmobile!
3.0 star property
Wisconsin Farmhouse Stay: Utv, Boat, Snowmobile!
Wisconsin Farmhouse Stay: UTV, Boat, Snowmobile!
Wisconsin Farmhouse Stay: UTV, Boat, Snowmobile!
Relax on the Sugar River in this beautiful newly renovated building
2.0 star property
The price is CA $254
CA $388 total
includes taxes & fees
Jun 22 - Jun 23
Relax on the Sugar River in this beautiful newly renovated building
Historic farmhouse with WiFi, dog-friendly, close to rec trails
2.0 star property
Historic farmhouse with WiFi, dog-friendly, close to rec trails
Don't see what you're looking for?
See all available properties in Orangeville
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.

Other types of properties in Orangeville you may be interested in

Super 8 by Wyndham Monroe WI
2.0 star property
9.0 out of 10, Wonderful, 617 reviews
"I was quite pleased "
The price is CA $87
CA $96 total
includes taxes & fees
Jun 30 - Jul 1
Super 8 by Wyndham Monroe WI
Country Inn & Suites by Radisson, Stockton, IL
2.5 star property
8.6 out of 10, Excellent, 488 reviews
"Nice and clean. Good value for your dollar."
The price is CA $95
CA $106 total
includes taxes & fees
Jul 1 - Jul 2
Country Inn & Suites by Radisson, Stockton, IL
Country Inn & Suites by Radisson, Freeport, IL
2.5 star property
9.0 out of 10, Wonderful, 704 reviews
"I liked that the staff was calm and friendly when there was an issue that happened. They are very clean and I will be booking again "
The price is CA $153
CA $170 total
includes taxes & fees
Jul 8 - Jul 9
Country Inn & Suites by Radisson, Freeport, IL
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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Orangeville. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Orangeville?

Yes, we offer vacation rentals close to popular attractions in Orangeville, or you can go with a more remote option if you'd like a relaxing place to stay.

What's the top vacation rental that Orangeville has to offer?

3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe: Visitors like this Orangeville vacation home rental. It is located in a rural location and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You can relax into your vacation 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 Roth Kase Cheese Factory, or get out into nature at a spot like Lake Le Aqua Na State Park. Historic Cheesemaking Center and Minhas Craft Brewery are a couple of places you'll find in the larger area.

What are vacation rentals like in Orangeville?

Vacation rentals are privately owned properties you can reserve for a few days or a quick weekend in Orangeville. Vacation rentals provide amenities like laundry facilities and kitchens so you'll have everything you want. If you're concerned about cleanliness, a vacation rental can offer a sense of security away from public hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for family trips.

Recent reviews of Orangeville properties
Expedia verified reviews