This detached house is located in Orangeville's North quarter, a short walk to the Lake Conservation Area and a brief drive to the Fork of the Credit and Hockley Valley parks and trails, with Blue Mountain and Toronto approximately 160 kilometres away. This detached house offers luxury boho style open-concept living for up to four guests, featuring two queen-sized bedrooms, a full bathroom, a well-equipped kitchen with modern appliances, and a 20.9 square metre rear deck overlooking the garden.
9.0 18 reviews
Orangeville
01/09 – 01/12
116 €/nighttotal: 10556 € (91 )
Gorgeous Cozy Cottage Besides A Bustling Stream, Surrounded By Gorgeous Greenery
1 2
cottage , Orangeville
This Orangeville riverfront cottage, situated 1 km from Hockley Valley Provincial Park and 2.2 km from Hockley Valley Resort, offers a tranquil escape near Theatre Orangeville and Island Lake Conservation Area (within 10 km). The 65 square metre self-catering property sleeps four guests in one bedroom and one bathroom, featuring a kitchenette, fireplace, WiFi, and access to outdoor barbecue grills and a garden.
Orangeville
08/07 – 04/09
2349 €/nighttotal: 136242 € (58 )
Woodlands
6 2
gîte , Caledon
This 6-bedroom, 5-bathroom holiday home in Caledon offers secluded accommodation on a 26-hectare private estate, located just 16 kilometres from Toronto Pearson International Airport and 5 kilometres from the Caledon Ski Club, with the Paintbrush golf course across the road and Caledon East a few minutes away. This property accommodates up to 11 guests and features an infinity pool, hot tub, fire pit, tennis court, separate 2-bedroom pool house, air hockey table, arcade games, Xbox, and a gourmet kitchen, all providing stunning views of the Mississauga and Toronto skylines from its elevated position along the Niagara Escarpment.
Orangeville
21/09 – 11/12
167 €/nighttotal: 13527 € (81 )
Spacious Cozy 4br Orangeville Home W/deck! 10-minute Walk To Headwaters Hospital
4 1
apartment , Orangeville
This family-friendly apartment in Orangeville is conveniently situated 240 metres from Island Lake Conservation Area and Theatre Orangeville, with Hockley Valley Resort and Heathlands Links at Osprey Valley also close by. This spacious 276 sqm residence offers four bedrooms, two and a half bathrooms, a living area with a fireplace, a fully equipped kitchen, in-unit laundry, a private terrace, a garden, and barbecue facilities, complemented by free Wi-Fi and air conditioning.
10 3 reviews
Orangeville
21/09 – 11/12
85 €/nighttotal: 6885 € (81 )
Brick House On Broadway - Butler Unit
1 1
apartment , Orangeville
This one-bedroom flat is located in a convenient district of Orangeville, offering easy access to local amenities and attractions. This welcoming accommodation for two guests includes a kitchen with a fridge, freezer, and microwave, and a garden, making it an ideal base for exploring Orangeville.
Orangeville
27/06 – 04/07
168 €/nighttotal: 1176 € (7 )
Entire Private 1 Bedroom Apartment In Alton Ont. A Place To Relax, Pet Friendly
1 2
apartment , Caledon
This private apartment in Caledon offers a rural escape, situated approximately 10 minutes by car from the main town's amenities and close to Orangeville, Erin, and Mono. This one-bedroom, one-bathroom flat accommodates up to three guests, featuring a full kitchen, cable TV, a stereo system, and controllable air conditioning and heating, with free parking for two vehicles on a 2-acre property.
Orangeville
01/09 – 31/12
177 €/nighttotal: 21417 € (121 )
The Crown Suite
1 1
apartment , Orangeville
This private upper-level flat is centrally located in Orangeville, offering convenient access to local amenities and a peaceful atmosphere. The Crown Suite accommodates up to three guests with one bathroom, a kitchen, air conditioning, and internet, and is a pet-friendly option for a comfortable stay.
10 1 review
Orangeville
08/07 – 04/09
199 €/nighttotal: 11542 € (58 )
Stay In The Heart Of Belfountain
1 2
apartment , Caledon
This three-bedroom apartment in Belfountain, Caledon, is situated in an 1888 heritage building, a short walk from local cafes and shops, and within a few minutes' drive of the Forks of the Credit Provincial Park and Belfountain Conservation Area. The self-catering flat, sleeping up to eight guests, includes a kitchen, air conditioning, parking, and a £25 nightly credit at the adjacent Belfountain cafe; nearby activities include hiking, biking, fishing, skiing, and golfing at top Ontario courses within 16km.
Orangeville
27/06 – 04/07
2297 €/nighttotal: 16079 € (7 )
Luxury, 4-bed House - Near Osprey Gc For Cdn Open
1 2
apartment , Caledon
This Caledon property, situated in a peaceful neighbourhood, offers easy access to local attractions within a short driving distance, its precise location requiring further specification for accurate distance calculations to landmarks. This 2700 sq ft (approximately 250 sq m) luxury dwelling boasts four bedrooms, two bathrooms, sleeps eight guests, and includes a golf practice area, hot tub, and a basement recreation area with fitness equipment.
Orangeville
30/07 – 04/08
418 €/nighttotal: 2090 € (5 )
Golf & Spa Retreat W/ Jacuzzi Near Tpc Toronto
3 2
apartment , Caledon
This countryside retreat is located in Alton village, Caledon, a short drive to Highway 10 for convenient access to Orangeville's amenities and nearby provincial parks such as Forks of the Credit Provincial Park and Belfountain Conservation Area, with Cheltenham Badlands also within reach. This spacious apartment accommodates up to 6 guests and offers a fully equipped kitchen, two living rooms, three bedrooms including a primary suite with an en-suite bathroom, air conditioning, a jacuzzi, a garden with a gazebo and fire pit, and private driveway parking for 8-10 vehicles.
9.8 8 reviews
Orangeville
08/07 – 04/09
815 €/nighttotal: 47270 € (58 )
10 Acres Private Bruce Trail Cottage For 14 Guests
1 2
apartment , Caledon
This Caledon cottage, located on a 10-acre property bordering the Bruce Trail and approximately 72 kilometres from Yorkdale Shopping Centre, offers creek access. The 3,700 sq ft property sleeps up to 14 guests in four bedrooms and three bathrooms, boasting a solarium, fully equipped kitchen, ample parking, and king-sized beds; nearby activities include hiking the Bruce Trail and exploring the Niagara Escarpment.
Orangeville
21/09 – 11/12
143 €/nighttotal: 11583 € (81 )
Hockley Valley Cozy Cottage With Waterfront Access
1 1
apartment , Orangeville
This two-bedroom flat is located in Mono, 3 kilometres from Orangeville, and backs onto the Nottawasaga River, offering a countryside escape with proximity to Mono Cliffs Provincial Park. This apartment sleeps up to four guests and features internet, air conditioning, and a kitchen, with year-round activities available including hiking and visiting local wineries and cideries.
Best family friendly Orangeville holiday rentals
Among the 39 accommodations in Orangeville, here are the 4 best family friendly rentals
10 1 review
Orangeville
21/09 – 11/12
276 €/nighttotal: 22356 € (81 )
Walk To Downtown Orangeville | Free Parking & Game
3 1
apartment , Orangeville
This apartment is located in a quiet district of Orangeville, offering a peaceful retreat away from the town's central bustle, approximately 3.5 kilometres from the Orangeville Town Hall. This property offers accommodation for up to six guests, featuring two bathrooms, air conditioning, and internet access, with a kitchen perfect for self-catering during your stay.
10 14 reviews
Orangeville
30/07 – 04/08
280 €/nighttotal: 1400 € (5 )
Little Blue Haven
1 2
apartment , Caledon
This three-bedroom flat in Caledon is located in the hills, offering direct access to nature trails and situated opposite Osprey Golf Course and Two Sons Restaurant, with Alton Mill Art Centre and Good Lot Brewing Company within easy reach. This accommodation for four guests features a king-sized bed on the main floor and a queen bed upstairs, with amenities including Wi-Fi, laundry facilities, a fully equipped kitchen with a dishwasher, and two smart TVs, all a 10-minute drive from boutique shopping in Orangeville and Erin.
9.9 57 reviews
Orangeville
30/07 – 04/08
133 €/nighttotal: 665 € (5 )
Beautiful Getaway In Orangeville
1 2
apartment , Orangeville
This apartment is situated in a peaceful neighbourhood just a short 800-metre walk from Island Lake Conservation Area, a popular spot for nature walks and outdoor activities, and a two-minute drive from Orangeville's town centre. The property boasts a spacious living area, a fully equipped kitchen, and a private deck with a barbecue, perfect for relaxing after a day exploring the surrounding area.
9.6 28 reviews
Orangeville
21/09 – 11/12
160 €/nighttotal: 12960 € (81 )
Private Hockley Valley Farmhouse
3 1
gîte , Orangeville
This three-bedroom farmhouse is located in Hockley Valley, just a short drive from Orangeville, offering easy access to the Bruce Trail, the Hockley Valley Conservation Area, and a variety of local attractions. The property enjoys excellent user, location, and cleanliness ratings, making it a top choice for travellers. The farmhouse comfortably accommodates up to seven guests and features a modern kitchen, a wood-burning fireplace, and super-fast Wi-Fi. Guests can enjoy a secluded country setting, access to nature, nearby attractions, and a range of adventurous activities, ensuring a memorable stay.
Best Orangeville holiday rentals with parking
Orangeville
30/07 – 04/08
401 €/nighttotal: 2005 € (5 )
Golf & Spa Retreat W/ Jacuzzi Near Tpc Toronto
3 2
apartment , Caledon
This detached house in Alton, Caledon, is situated in a peaceful rural area offering countryside views and easy access to Highway 10, placing it a short drive from Orangeville's amenities and within proximity of Forks of the Credit Provincial Park, Belfountain Conservation Area, Cheltenham Badlands, and Island Lake Conservation Area. Spanning 223 square meters, this residence accommodates up to six guests with three bedrooms, two bathrooms, two living rooms, a fully equipped kitchen, and outdoor amenities including a deck, gazebo, jacuzzi, and fire pit, alongside private parking for 8-10 vehicles.
9.3 60 reviews
Orangeville
30/07 – 04/08
639 €/nighttotal: 3195 € (5 )
Charming And Peaceful Retreat With Hot Tub
1 2
apartment , Caledon
This six-bedroom Caledon house, sleeping up to twelve guests, is situated in a peaceful neighbourhood, approximately 14km from the TPC Toronto Osprey Valley Golf Course, 9km from Hockley Valley Resort, and within easy driving distance of other attractions including Caledon Ski Club and Island Lake Conservation Area. The property boasts a fully equipped kitchen with dishwasher and wine fridge, a spacious dining room, three renovated bathrooms, a hot tub, and a large garden, perfect for families or groups seeking a self-catering base for exploring Caledon's amenities.
Orangeville
27/06 – 04/07
367 €/nighttotal: 2569 € (7 )
Luxurious Farmhouse On 100 Acres- 45 Mins From North Of Gta
3 2
manor house , Amaranth
This Amaranth farmhouse, a 12-minute (19km) drive from Mono Cliffs Provincial Park and 17-minute (27km) drive from Island Lake Conservation Area, offers a convenient base for exploring rural Ontario. The 372 square metre property boasts four bedrooms, three bathrooms, sleeps ten guests, and includes a tennis court, Wi-Fi, and a fully equipped kitchen alongside access to nearby winter sports such as snowboarding and snowmobiling.
10 1 review
Orangeville
08/07 – 04/09
627 €/nighttotal: 36366 € (58 )
Perfect 10 Acres Private Quiet Property For Small Events & Family Gatherings
4 2
cottage , Caledon
Vintage Cottage Retreat, a 4-bedroom property sleeping 14, is situated in Caledon, Ontario, approximately 72km from Yorkdale Shopping Centre and conveniently located near Forks of the Credit Provincial Park and the Bruce Trail. This 3,700 sq ft holiday home boasts a full kitchen with microwave and dishwasher, 4 bathrooms, a solarium, terrace, garden, parking, air conditioning, and a wood-burning fireplace; it also offers 10 acres of land ideal for camping, stargazing, and small events.
Frequently asked questions about holiday rentals in Orangeville
What are the top family-friendly attractions in Orangeville?
The Orangeville Public Library has lots of fun events and activities for children, and the Island Lake Conservation Area has fantastic walking trails and a playground. For a bit of history, the Orangeville Museum is a great option for families.
What are the best Airbnb and holiday rentals in Orangeville?
When is the best time to book a vacation rental in Orangeville?
The best time to book a vacation rental in Orangeville is during the shoulder seasons, like spring or autumn. You'll get better rates and avoid the crowds, plus the weather is usually pleasant.
What events or festivals should visitors check out in and around Orangeville?
The Orangeville Farmers' Market is a popular event on Saturdays, and the Orangeville Fall Fair in September is a great way to experience local culture. There are also several festivals throughout the year, like the Orangeville Blues & Jazz Festival in June.
What are the best holiday rentals with a pool in Orangeville?
What are the best budget-friendly activities in Orangeville?
A walk along the scenic trails at Island Lake Conservation Area is free and a great way to enjoy the outdoors. You can also visit the Orangeville Public Library or browse the shops on Broadway without spending a penny.
What are the best rentals for families and kids in Orangeville?
What are the best restaurants with local dishes in Orangeville?
For a taste of local cuisine, head to The Cornerstone Pub or The Mill Street Grill. Both offer classic Canadian dishes with a modern twist. You can also find some great Italian food at La Piazza.
What are the best rentals or Airbnbs with a jacuzzi in Orangeville?
What are the best walking or cycling routes in Orangeville?
The trails at Island Lake Conservation Area are perfect for walking or cycling. The Credit River Trail is also a great option, offering scenic views and plenty of wildlife.
Are there pet-friendly attractions in Orangeville?
Yes, many attractions in Orangeville are pet-friendly. You can walk your dog on the trails at Island Lake Conservation Area, or take them for a stroll along Broadway. Many of the restaurants also have outdoor seating areas that welcome pets.
What are the benefits of choosing a vacation rental in Orangeville?
Vacation rentals offer more space and privacy than a hotel, often at a lower cost. You'll also have access to a kitchen and laundry facilities, making it easier to settle in and feel at home.
What are the top sports attractions and facilities in Orangeville?
The Orangeville Tennis Club has several courts, and the Orangeville Skating Club offers ice skating lessons and public skating sessions. The town also has several parks and green spaces where you can enjoy a game of basketball or soccer.
Destinations nearby
Best Orangeville holiday rentals with a balcony
8.1 1501 reviews
Orangeville
30/07 – 04/08
264 €/nighttotal: 1320 € (5 )
Hockley Valley Resort
1 2
resort , Orangeville
Hockley Valley Resort in Orangeville offers a family-friendly escape, located under 15 minutes by car from Orangeville and the Hockley Valley Provincial Nature Reserve, with Luther Marsh Conservation area approximately 100 kilometres away. This establishment boasts an 8,000 sq ft spa, indoor and outdoor swimming pools, an 18-hole golf course, a ski hill with 16 runs, and on-site dining at the farm-to-table restaurant, Cabin, and the lobby bar, Babbo, with Adamo Estate Winery just 1 kilometre down the road.
Orangeville
21/09 – 11/12
324 €/nighttotal: 26244 € (81 )
Walk To Downtown Orangeville With Free Parking & Games
3 1
house , Orangeville
This Orangeville holiday home is a 7-minute walk from Theatre Orangeville and is located approximately 48 kilometres from Wild Water Kingdom. This property accommodates up to 11 guests with 3 bedrooms and 3 bathrooms, featuring a fully equipped kitchen, Wi-Fi, an indoor play area, and a fireplace, with laundry services and free parking available.
Best pet friendly Orangeville holiday rentals
Among the 39 accommodations in Orangeville, here are the 4 best pet friendly rentals
9.3 12 reviews
Orangeville
08/07 – 04/09
162 €/nighttotal: 9396 € (58 )
Spacious Country Home-5br Near Orangeville
5 2
gîte , Amaranth
This five-bedroom, two-bathroom Amaranth property, ideal for large groups, offers ample parking and a detached garage/workshop. The self-catering apartment boasts a spacious open-plan living area, high-speed Wi-Fi, a gas fireplace, and a large one-acre plot with a patio, accommodating up to ten guests.
Orangeville
27/06 – 04/07
63 €/nighttotal: 441 € (7 )
Ballo - Guesthouse
1 2
house , Orangeville
This private, newly renovated suite in Orangeville offers a separate entrance and is located in a quiet residential area, just 1.5 kilometres from downtown shops, Theatre Orangeville, Island Lake trails, and Hockley Valley skiing. This modern accommodation for two features a fully-equipped kitchen with quartz counters, a double bedroom, a spa-style bathroom with a glass shower, and provides internet access, making it ideal for couples or remote workers seeking mid-term stays with easy access to local attractions and outdoor activities.
Orangeville
08/07 – 04/09
163 €/nighttotal: 9454 € (58 )
Newly Renovated 1 Bedroom Apartment In Alton, Ontario
1 2
apartment , Caledon
This private one-bedroom flat offers a secluded country experience in rural Caledon, located approximately 16 kilometres from Orangeville, Erin, and Mono, with convenient access to Forks of the Credit Provincial Park and Belfountain Conservation Area. This self-contained dwelling accommodates up to three guests with a queen bed and a single pull-out sofa, featuring a full kitchen, air conditioning, cable TV, and free parking for two vehicles, making it ideal for those seeking a peaceful retreat with easy access to local amenities and natural attractions.
Orangeville
27/06 – 04/07
96 €/nighttotal: 672 € (7 )
Country Side Greenery
1 2
apartment , Orangeville
This private apartment is located on over 4 acres, offering a secluded setting just outside Orangeville, with easy access to the Bruce Trail and Hockley. This spacious accommodation, suitable for two guests, features a separate entrance, a kitchen, air conditioning, and allows pets, providing ample room and privacy for your stay.