Orangeville holiday lettings

We found 76 holiday rentals — enter your dates for availability

Discover a selection of 11 homes and other holiday rentals in Orangeville that are perfect for your trip. Holiday homes provide the amenities that you need and want for your family, friends or furry companion, such as cable TV and a washer and dryer. Whatever you're looking for, you'll be able to choose a property to rent that has what everyone needs, including accessible or non-smoking choices.

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Why visit Orangeville

  • Picturesque Heritage District: Stroll through charming streets filled with unique shops, galleries, and cafés.
  • Lively local festivals: Experience vibrant events that celebrate Orangeville's rich culture and community spirit.
  • Outdoor adventures: Explore nature reserves and national parks ideal for hiking, biking, and relaxing.
  • Family-friendly atmosphere: Enjoy a welcoming environment perfect for families seeking quality time together.
  • Variety of accommodation options: Choose from charming homes, cosy apartments, and rustic cabins for a memorable stay.

Popular types of accommodation in Orangeville

Orangeville offers a delightful variety of vacation rentals to suit every traveller's needs. Whether you're seeking a charming private vacation home, a cosy apartment, or a rustic cabin, you'll find the perfect base for your getaway. Popular choices include Orangeville house rentals and spacious apartments, including convenient bedroom apartments for families or groups. Explore your options and enjoy a memorable stay in this picturesque locale.

  • Houses: The top choice for holiday rentals in Orangeville, offering spacious and comfortable settings ideal for families or groups.
  • Apartments: A popular selection for couples and solo travellers, providing convenient amenities and a home-like atmosphere.
  • Cabins: A charming option for those seeking a rustic escape, nestled in nature’s embrace.
  • Condos: These modern accommodations offer a blend of comfort and luxury, perfect for a stylish retreat.
  • Cottages: A delightful choice for a quaint and cosy getaway, often surrounded by picturesque landscapes.**

Top attractions in and around Orangeville

Orangeville, Ontario, is perfect for outdoor enthusiasts and adventure seekers, offering a variety of attractions such as nature reserves, fairgrounds, and national parks. Whether travelling with family or seeking cultural experiences, you'll find plenty to explore in and around this charming town. From scenic landscapes to engaging activities, Orangeville promises a delightful escape for all types of visitors.

  • Island Lake Conservation Area: This picturesque reserve within Orangeville offers a serene escape with its scenic trails and tranquil lake. Ideal for leisurely walks, birdwatching, and picnics, it is a perfect spot for nature enthusiasts.
  • Alton Mill Arts Centre: Located 2.5km from Orangeville, this charming arts centre showcases local artisans and hosts various cultural events. Explore the galleries and enjoy workshops in a historic mill setting, celebrating creativity.
  • Hockley Valley Provincial Park: Situated 2.5km from Orangeville, this expansive park is a haven for outdoor adventurers. Enjoy hiking, cycling, and breathtaking views of the stunning scenery, making it an ideal spot for nature lovers.

Things to do recommended for couples

For a romantic getaway in Orangeville, consider the luxurious Caledon Ski Club, just 5.6km away, or the elegant Caledon Country Club, 8.1km distant. For a more sporty vibe, head to Mansfield Ski Club, located 15.6km from town, perfect for couples who enjoy skiing together.

Things to do recommended for families

Families visiting Orangeville can explore the natural beauty of Mono Cliffs Provincial Park, unwind at the Cheltenham Badlands, and enjoy outdoor activities at Albion Hills Conservation Area, all offering a wonderful blend of relaxation and adventure suitable for all ages.

Things to do recommended for groups

Groups visiting Orangeville can enjoy a round of golf at Osprey Valley Golf, experience the vibrant performances at Theatre Orangeville, and explore local produce at Downey's Farm Market, all while soaking in the charming atmosphere of this delightful Canadian town.

What do I need to keep in mind when booking a vacation in 'Orangeville

If you’re travelling with a group, family, pets, or planning extended stays, it’s important to filter your options based on your key priorities. Here are some helpful booking tips for using Vrbo.

  • Traveling to Orangeville with a group: Think about how many bedrooms you'll require, as well as features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily refine your search for all of these options and more on Vrbo.
  • Traveling to Orangeville with young kids: Travelling with young children can be quite demanding. It's essential to prioritise their comfort and safety, along with suitable facilities, like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Orangeville: For many, a family holiday wouldn’t feel complete without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and cosy beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Orangeville: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Orangeville

Orangeville, Ontario, offers a delightful mix of outdoor adventures and charming community vibes. Explore the picturesque Heritage District and enjoy the lively festivals that showcase local culture. The friendly atmosphere makes it a perfect getaway for families, while Eastview Crescent boasts some of the best houses in the area. With ample opportunities for recreation, Orangeville is an ideal destination for those seeking a relaxing yet vibrant vacation experience.

  • Mono: Situated approximately 3.7km from Orangeville, Mono is a delightful city that beckons adventurers and sports enthusiasts alike. Known for its stunning landscapes and outdoor activities, Mono offers a range of attractions, including ski resorts and golf courses. Nature lovers will appreciate the local nature reserves and parks, while the serene lakes provide a perfect backdrop for a tranquil day out. Whether you're hitting the slopes in winter or enjoying a round of golf in the summer, Mono promises an exhilarating travel experience for all.
  • Mono Mills: This charming village, located around 3.7km from Orangeville, is an outdoor enthusiast's paradise. Mono Mills is famed for its vibrant recreational scene, offering a variety of sports and adventure activities. Visitors can enjoy skiing and golfing, with several well-maintained venues nearby. The village is also home to lovely urban parks and picturesque lakes, making it an ideal spot for a family picnic or a leisurely stroll. With its welcoming atmosphere and abundance of outdoor pursuits, Mono Mills is a must-visit for anyone seeking adventure.
  • Caledon: Approximately 7.5km from Orangeville, Caledon is a city that effortlessly combines outdoor adventure with natural beauty. Known for its extensive parks and nature reserves, Caledon is perfect for those looking to escape the hustle and bustle of city life. The area is popular for skiing and golfing, with numerous resorts catering to sports enthusiasts. Visitors can explore the scenic lakes and lush landscapes, making it a splendid destination for hiking, cycling, or simply enjoying a leisurely day outdoors. Caledon's charm lies in its ability to provide both relaxation and adventure.

Best time to go to Orangeville

If you're planning a trip to Orangeville, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April, July and September, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January19.9°F (-6.7°C)Light RainMostly CloudyAverageSlightly Low
February20.5°F (-6.4°C)Light RainMostly CloudyAverageSlightly Low
March30.0°F (-1.1°C)Light RainMostly CloudyAverageAverage
April41.0°F (5.0°C)Light RainMostly CloudySlightly HighSlightly Low
May54.3°F (12.4°C)Light RainMostly SunnyAverageAverage
June62.4°F (16.9°C)Light RainMostly SunnyAverageSlightly High
July68.0°F (20.0°C)Light RainMostly SunnySlightly HighSlightly High
August66.7°F (19.3°C)Light RainMostly SunnyAverageSlightly High
September60.3°F (15.7°C)Light RainMostly SunnySlightly HighAverage
October48.2°F (9.0°C)Light RainMostly CloudySlightly LowAverage
November36.3°F (2.4°C)Light RainMostly CloudySlightly LowAverage
December27.7°F (-2.4°C)Light RainMostly CloudySlightly LowAverage

Booking with Vrbo is a breeze

Are you hoping to cut costs on your next getaway? Being flexible with your travel dates can be beneficial, as prices often fluctuate. Additionally, consider booking a longer stay to take advantage of considerable savings. To discover a Vrbo property that aligns with your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board offers a handy platform for planning your journeys, allowing you to start new trips, resume from where you paused, or manage and view your existing arrangements. You'll see the properties you've saved or booked neatly organised into categories: Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Delight in the picturesque landscape of Orangeville

Enjoy the monuments and other features of Orangeville. This city's hockey games, skiing and sightseeing draw many visitors. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Sightseeing in and around Orangeville

Are you searching for attractions to see in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Orangeville a one-of-a-kind holiday spot. These are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Hockley Valley Resort (4.5 mi / 7.2 km)
  • Osprey Valley Golf (5.5 mi / 8.8 km)
  • Heathlands Links at Osprey Valley (6 mi / 9.7 km)
  • Caledon Ski Club (9.1 mi / 14.6 km)
  • Caledon Country Club (12.5 mi / 20.2 km)
  • Albion Hills Conservation Area (13.2 mi / 21.2 km)

Exploring the natural landscape of Orangeville

Whether you're looking for fun outdoor activities or just want to appreciate the scenery, Orangeville is a great place to spend some time outside. Here are some of the area’s most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • Belfountain Conservation Area (9.6 mi / 15.4 km)
  • Cheltenham Badlands (12.5 mi / 20.2 km)
  • Terra Cotta Conservation Area (15.3 mi / 24.6 km)
  • Island Lake Conservation Area (0.8 mi / 1.3 km)
  • Albion Hills Conservation Area (13.2 mi / 21.2 km)
  • Forks of the Credit Provincial Park (8.3 mi / 13.3 km)

Transport options to and around Orangeville

The nearest airport is in Toronto, ON (YYZ-Pearson Intl.), located 29.2 mi (47 km) from the city centre. If you can't find a flight that's convenient for your trip, you might consider flying into Kitchener, ON (YKF-Region of Waterloo Intl.), which is 35.2 mi (56.7 km) away.

Frequently asked questions

What is the best area to stay in Orangeville when booking a holiday rental?
When considering the best area to stay in Orangeville, Ontario, it's hard to overlook the charm of the town centre. This vibrant neighbourhood is known for its picturesque streets lined with quaint shops, cafes, and restaurants, making it a delightful place to explore. A top attraction in this area is the Orangeville Museum, which showcases the local history and culture, providing visitors with a deeper understanding of the region. Additionally, the nearby Theatre Orangeville offers an array of performances and events that cater to various tastes in the arts.

Another appealing option is the area around the Island Lake Conservation Area. This beautiful natural setting is superb for outdoor enthusiasts, offering trails for hiking and biking, as well as opportunities for fishing and birdwatching. The serene environment provides a peaceful retreat, while still being close to the amenities of the town.

In Orangeville, there is a diverse range of properties available for holiday rentals, suiting different preferences and budgets. Whether you prefer a cosy cottage or a modern apartment, you'll find something that suits your needs in either of these lovely neighbourhoods.
How much does it cost to rent a holiday home in Orangeville?
Prices for holiday rentals in Orangeville vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Orangeville to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Orangeville holiday house rentals?
You can find great discounts on house rentals in Orangeville on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of holiday rental accomodation in Orangeville?
In Orangeville, holiday houses are the most popular type of holiday rental, with approximately 30 available throughout the area. These homes typically offer spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor areas where guests can relax and enjoy the surrounding nature. They are particularly suited for families or groups seeking a comfortable home base for exploring the local attractions. Additionally, there are around 18 apartments available, which provide a more compact and convenient option for travellers. These apartments usually include essential amenities such as kitchens and living spaces, making them ideal for shorter stays or couples.
Are there any family house rentals in Orangeville?
In Orangeville, Ontario, there are several family-friendly house rentals available, making it a great choice for those travelling with children. The properties typically feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where kids can enjoy themselves. Many homes come with amenities like Wi-Fi and air conditioning, ensuring a comfortable stay for everyone.

This charming town offers access to local parks, such as the scenic Island Lake Conservation Area, which is superb for outdoor activities and picnics. Additionally, the area boasts various family attractions, including the historic downtown with its quaint shops and restaurants.
Can I find long-stay holiday rentals in Orangeville?
A long-stay holiday rental in Orangeville is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Orangeville?
In Orangeville, there are several pet-friendly house rentals available for those looking to travel with their furry companions. Many of these properties provide amenities such as spacious backyards, fully equipped kitchens, and comfortable living areas, making them ideal for families or groups.

The town is surrounded by beautiful parks and green spaces, superb for leisurely walks with pets. Nearby, the Island Lake Conservation Area offers scenic trails and a serene environment, allowing for enjoyable outdoor activities. Additionally, the town hosts various pet-friendly cafes and shops, enhancing the overall experience for travellers with pets.
Are there any remote work holiday rentals in Orangeville?
In Orangeville, Ontario, there are a variety of remote work holiday rentals available, with around 45 options to choose from. This charming town offers a blend of natural beauty and a vibrant community, making it an ideal spot for those looking to work remotely while enjoying a picturesque setting. Many properties come equipped with amenities such as high-speed internet and Wi-Fi, ensuring a reliable connection for work needs.

Travellers can expect comfortable living spaces, often featuring dedicated work areas, fully equipped kitchens for self-catering, and inviting outdoor spaces to relax after a day of work. The town itself is known for its lovely parks, quaint shops, and local dining options, providing ample opportunities to unwind and explore during downtime. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Orangeville holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Orangeville with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Orangeville?
In Orangeville, popular rental amenities include well-equipped kitchens, which allow guests to prepare their own meals. Many properties also feature decks or patios, great for enjoying the outdoors and soaking up the local atmosphere. A coffee or tea maker is commonly found in the rentals, ensuring that guests can enjoy a warm beverage at their leisure. Onsite parking is another convenient amenity that travellers can expect, providing easy access to their accommodations. Additionally, many rentals come with fireplaces, creating a cozy and inviting atmosphere, especially during the colder months.
When is the best time to visit Orangeville for a holiday rental?
The best time to visit Orangeville for a holiday rental is during the peak season from July to September. This vibrant period attracts visitors eager to enjoy outdoor activities, local festivals, and the stunning natural beauty of the surrounding area. With warm temperatures averaging between 20 to 30 degrees Celsius, it's an ideal time for hiking and exploring the picturesque trails of the nearby Mono Cliffs Provincial Park.

July stands out as the most popular month, where you can experience a lively option filled with community events and bustling markets. Families and adventure seekers alike flock to Orangeville, making it an exciting time to engage with fellow travellers and partake in the various activities on offer.

For those looking for a more budget-friendly option, consider visiting in November. This month may be quieter, but it offers a unique charm with the onset of autumn, allowing you to enjoy the beautiful fall colours and serene landscapes without the crowds. It's a great time to explore local shops, cosy up in a café, or take leisurely walks through the scenic parks.

Ultimately, your choice of when to visit Orangeville hinges on whether you prefer the energetic buzz of peak season or the tranquil beauty of the shoulder months.
How early should I book a Orangeville holiday rental?
Book your Orangeville holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Orangeville?
In Orangeville, visitors can enjoy a variety of attractions that showcase the town's charm and natural beauty. The historic downtown area is superb for a leisurely stroll, with quaint shops, cafes, and local art galleries. The Orangeville Farmers' Market, held on Saturdays, offers fresh produce and artisanal goods, providing a taste of the local culture.

For outdoor enthusiasts, the Island Lake Conservation Area is a popular spot that features scenic trails for hiking and cycling, as well as opportunities for birdwatching and picnicking by the water. The nearby Mono Cliffs Provincial Park offers stunning views and more extensive hiking trails, making it ideal for those seeking adventure in nature.

Cultural attractions include the Theatre Orangeville, where visitors can enjoy a range of performances from drama to comedy, showcasing local talent.
Can I change or cancel my Orangeville home rental booking on Vrbo?
To find Orangeville holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Orangeville holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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