Orangeville Vacation Rentals

Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Orangeville vacation rentals

A spacious living area with a wooden dining table, a sofa, and a hanging chair. There are large windows providing natural light and a view of the outside.

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

MJ's Penthouse ,a piece of paradise on Monroe's historic square
Monroe
10.0 out of 10, Exceptional, (115 reviews)
"The Penthouse is beautiful and the location is unbeatable! We had a wonderful stay and can't wait to come back."
United States
Andie
$231 nightly
The price is $253
Nov 8 - Nov 9
Total with taxes and fees
MJ's Penthouse ,a piece of paradise on Monroe's historic square
A spacious kitchen with wooden cabinets, a central island, and a dining area with a table and chairs.

2. Lookout Loft over the Monroe Square

Lookout Loft over the Monroe Square
Monroe
10.0 out of 10, Exceptional, (4 reviews)
"Great property and host! Would stay there again."
United States
Ann S.
$206 nightly
The price is $225
Nov 9 - Nov 10
Total with taxes and fees
Lookout Loft over the Monroe Square
A red cabin with a porch, surrounded by trees.

3. Peace & Simplicity in a Little Red Cabin on the Farm

Peace & Simplicity in a Little Red Cabin on the Farm
Lena
10.0 out of 10, Exceptional, (45 reviews)
"Great place to stay"
United States
Mike G.
$148 nightly
The price is $157
Nov 15 - Nov 16
Total with taxes and fees
Peace & Simplicity in a Little Red Cabin on the Farm
A bedroom with a floral bedspread, a window with blinds, and a chair.

4. Quiet Charm Near Recreation Park

Quiet Charm Near Recreation Park
Monroe
$217 nightly
The price is $237
Nov 15 - Nov 16
Total with taxes and fees
Quiet Charm Near Recreation Park
A wooden deck with potted plants, a hot tub, and a swimming pool.

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

Quite- relaxing country living with pool/hot tub and sauna!
Pecatonica
10.0 out of 10, Exceptional, (20 reviews)
"Great place to stay "
United States
Dulce C.
$289 nightly
The price is $306
Nov 8 - Nov 9
Total with taxes and fees
Quite- relaxing country living with pool/hot tub and sauna!
A large, two-story log cabin with a stone chimney, a front porch with outdoor seating, and a snow-covered yard leading to a fire pit.

6. Lake Cabin | Sauna · River · Game Room

Lake Cabin | Sauna · River · Game Room
Brodhead
9.8 out of 10, Exceptional, (15 reviews)
"We love this property on the Sugar River. Very spacious, rustic but with all the modern amenities. Beautiful view of the water and lots of wildlife in area. "
United States
Lisa and Peter R.
$672 nightly
The price is $709
Nov 9 - Nov 10
Total with taxes and fees
Lake Cabin | Sauna · River · Game Room
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

An indoor swimming pool with a wooden ceiling, tiled walls, and a clear view of the outdoors through a window.
Super 8 by Wyndham Monroe WI

Super 8 by Wyndham Monroe WI

Super 8 by Wyndham Monroe WI
Monroe

10/10 Excellent

The beds were very comfortable. The room was clean. The staff very pleasant.
United States
Tami
Reviewed April 29, 2025
Super 8 by Wyndham Monroe WI

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 $156 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.

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?

MJ's Penthouse ,a piece of paradise on Monroe's historic square: Visitors like this Orangeville vacation home rental. It is located in the city center 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 Sugar River Raceway, or get out into nature at a spot like Oakdale Nature Preserve. National Historic Cheesemaking Center Museum 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.