Orangeville holiday rentals

We found 73 holiday rentals — enter your dates for availability
Discover a selection of 12 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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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)
  • Albion Hills Conservation Area (13.2 mi / 21.2 km)
  • Caledon Country Club (12.5 mi / 20.2 km)
  • Heathlands Links at Osprey Valley (6 mi / 9.7 km)
  • Caledon Ski Club (9.1 mi / 14.6 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)
  • Albion Hills Conservation Area (13.2 mi / 21.2 km)
  • Terra Cotta Conservation Area (15.3 mi / 24.6 km)
  • Island Lake Conservation Area (0.8 mi / 1.3 km)
  • Luther Marsh Conservation Area (15.5 mi / 25 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.
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.
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 Stayz.
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.
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.
Are all fees included in the Orangeville holiday homes prices shown on Stayz?
Stayz 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.
Are there any Orangeville holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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.
Are there any discounts for Orangeville holiday homes?
You can find great discounts on holiday homes in Orangeville on Stayz, 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.
Can I change or cancel my Orangeville holiday home booking on Stayz?
To find Orangeville holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Orangeville?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz'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 favourites, and build the perfect itinerary together.
How early should I book a Orangeville holiday home?
Book your Orangeville holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Orangeville?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Orangeville to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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