This private, self-contained ground-level suite is situated on a quiet street in Orangeville, offering convenient access to the local hospital and ski hills, with the countryside just a short distance away. This heated apartment for two features a fully equipped kitchen, a separate bedroom with a queen-size bed, a modern walk-in shower, and complimentary Wi-Fi, with hosts readily available on the property.
10 1 review
Orangeville
30/07 – 04/08
NZ$295/nighttotal: NZ$1475 (5 )
Memory Lane
1 2
apartment , Orangeville
This ground-floor flat is located in a central Orangeville district, offering direct walking access to local shops and eateries within 500 meters of the town centre. This self-contained accommodation for two guests features a kitchen, air conditioning, and one bathroom, providing a comfortable base for exploring Orangeville.
10 177 reviews
Orangeville
30/07 – 04/08
NZ$273/nighttotal: NZ$1365 (5 )
Hottub & Private Suite - Casa Facciolo
1 2
apartment , Orangeville
This one-bedroom house is situated in a safe, central neighbourhood in Orangeville, just a short walk from the historic downtown with its boutique shops and restaurants, and within minutes of both Tony Rose and Alder Arenas. The house offers a comfortable living space with a fireplace, TV, dining area, kitchenette, and laundry, and can accommodate up to four guests.
Orangeville
01/09 – 01/12
NZ$2153/nighttotal: NZ$195923 (91 )
Private Caledon Retreat With Pool & Hot Tub
1 2
apartment , Caledon
This Caledon flat offers a private resort-style retreat in a peaceful countryside setting, just a few minutes' drive from Orangeville's shops, restaurants, golf courses, and scenic trails. Boasting five bathrooms and capacity for fourteen guests, this apartment provides a heated swimming pool, hot tub, fitness centre, and a landscaped backyard for outdoor enjoyment, with internet and air conditioning included.
9.9 342 reviews
Orangeville
30/07 – 04/08
NZ$397/nighttotal: NZ$1985 (5 )
The Trails Retreat (Private Cabin)
1 2
cabin , Orangeville
This private cabin is situated near Orangeville, just a short distance from the Bruce Trail and Hockley Ski & Resort, offering a peaceful escape surrounded by nature. It has received excellent ratings for its location, cleanliness, and overall experience. The studio comfortably accommodates up to four guests and features a kitchen with a fridge and microwave. Enjoy access to a shared swimming pool, a private garden, and a range of activities including yoga classes, chef-prepared meals, and discounts for longer stays.
9.8 8 reviews
Orangeville
08/07 – 04/09
NZ$1622/nighttotal: NZ$94076 (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.
9.3 12 reviews
Orangeville
08/07 – 04/09
NZ$322/nighttotal: NZ$18676 (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.
9.7 12 reviews
Orangeville
01/09 – 31/12
NZ$210/nighttotal: NZ$25410 (121 )
The Enchanted Cottage
1 1
cabin , Orangeville
This charming cottage is situated close to the centre of Orangeville, offering easy access to the town's amenities and attractions. The surrounding area is peaceful and green, with a lively stream flowing nearby. The cottage has one bathroom and can comfortably accommodate up to four guests. It is equipped with a kitchen, air conditioning, parking, and internet access, providing all the essentials for a relaxing stay.
10 1 review
Orangeville
27/06 – 04/07
NZ$1634/nighttotal: NZ$11438 (7 )
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.
8.9 7 reviews
Orangeville
21/09 – 11/12
NZ$605/nighttotal: NZ$49005 (81 )
Spectacular Estate Pristine 100 Acres Private Lake
4 1
apartment , Caledon
This luxurious four-bedroom, four-bathroom apartment is located in Caledon, Ontario, a short drive (approximately 11km) from Orangeville Square and within walking distance (800m) of the Upper Credit Conservation Area. The self-catering property sleeps eight guests and boasts a heated pool, sauna, on-site gym, BBQ area, and access to scenic trails and a tranquil pond with paddleboards, all within a private 40-hectare estate.
Orangeville
30/07 – 04/08
NZ$394/nighttotal: NZ$1970 (5 )
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
08/07 – 04/09
NZ$14329/nighttotal: NZ$831082 (58 )
Peak House
1 2
apartment , Caledon
This five-bedroom house is located in the Caledon countryside, just 64 kilometres from Toronto city centre and a short drive from the village of Caledon. The property boasts a private outdoor oasis with a swimming pool, hot tub, and fire pit, perfect for relaxing and entertaining, as well as a spacious interior with five bathrooms, a sauna, and a bar.
Best family friendly Orangeville holiday rentals
Among the 39 accommodations in Orangeville, here are the 4 best family friendly rentals
8.0 3 reviews
Orangeville
21/09 – 11/12
NZ$341/nighttotal: NZ$27621 (81 )
Spacious Cozy 4br Home W/patio Deck—near Hospital!
4 1
apartment , Orangeville
This four-bedroom house in Orangeville is situated 800 metres from Headwaters Health Care Centre and 8 kilometres from Mount Alverno Luxury Resorts, offering convenient access to local amenities and attractions including Island Lake Conservation Area and Broadway boutiques. This spacious property, ideal for families and groups of up to ten, features air conditioning, a jacuzzi, a garden, a fitness centre, parking, a fully equipped kitchen, a patio with a BBQ, and complimentary Wi-Fi.
9.9 57 reviews
Orangeville
30/07 – 04/08
NZ$264/nighttotal: NZ$1320 (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.
10 14 reviews
Orangeville
30/07 – 04/08
NZ$557/nighttotal: NZ$2785 (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.
Orangeville
21/09 – 11/12
NZ$332/nighttotal: NZ$26892 (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.
Best Orangeville holiday rentals with parking
Orangeville
27/06 – 04/07
NZ$430/nighttotal: NZ$3010 (7 )
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.
10 5 reviews
Orangeville
30/07 – 04/08
NZ$329/nighttotal: NZ$1645 (5 )
The Green Lodge - Upper Level Raised Bungalow
1 2
bungalow , Orangeville
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.
8.1 1501 reviews
Orangeville
27/06 – 04/07
NZ$674/nighttotal: NZ$4718 (7 )
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.
9.6 16 reviews
Orangeville
30/07 – 04/08
NZ$294/nighttotal: NZ$1470 (5 )
Brick House On Broadway - Coach House
1 2
house , Orangeville
This restored historic coach house, once part of Lester B. Pearson's grandparents' property, offers a private retreat in Orangeville, a short 500-meter walk from the town's historic core with its shops and restaurants, and is conveniently located for access to Hockley Valley, Mono Cliffs, and Island Lake hiking trails. This one-bedroom, one-bathroom dwelling accommodates two guests and features a fully equipped kitchen with a fridge, freezer, and microwave, air conditioning, internet, and parking, with an outdoor side yard complete with a picnic table for enjoying the mature tree surroundings.
Frequently asked questions about holiday rentals in Orangeville
What are the top family-friendly attractions in Orangeville?
The Orangeville Public Library has a great children's section and hosts regular events, and the Island Lake Conservation Area is perfect for a picnic or a walk with the kids.
What are the best Airbnb and holiday rentals in Orangeville?
When is the best time to book a vacation rental in Orangeville?
To get the best deals, you should book your rental at least a few months in advance, especially if you're planning to visit during peak season in the summer.
What events or festivals should visitors check out in and around Orangeville?
The Orangeville Farmers' Market is a highlight, running from June to October, and the annual Ribfest in July is a popular event with live music and plenty of food.
What are the best holiday rentals with a pool in Orangeville?
What are the best budget-friendly activities in Orangeville?
The Orangeville Public Library has free events and activities, and you can enjoy a scenic walk or bike ride along the trails at the Island Lake Conservation Area without spending a penny.
What are the best rentals for families and kids in Orangeville?
What are the best walking or cycling routes in Orangeville?
The 'Island Lake Trail' is a popular choice for a leisurely walk or bike ride, and the 'Orangeville Creek Trail' winds its way through the town, offering beautiful scenery and a glimpse of local history.
Are there pet-friendly attractions in Orangeville?
The Island Lake Conservation Area is pet-friendly, and many of the cafes and restaurants in town have outdoor seating where you can enjoy a meal with your furry companion.
What are the benefits of choosing a vacation rental in Orangeville?
Vacation rentals offer more space and privacy compared to hotels, and you can often find rentals with unique features like a backyard or a patio.
What are the top sports attractions and facilities in Orangeville?
The 'Orangeville Tennis Club' is a popular spot for tennis enthusiasts, and the 'Orangeville Skating Club' offers ice skating lessons and public skating sessions.
Destinations nearby
Best Orangeville holiday rentals with a balcony
Orangeville
21/09 – 11/12
NZ$645/nighttotal: NZ$52245 (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.
Orangeville
27/06 – 04/07
NZ$716/nighttotal: NZ$5012 (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.
Best pet friendly Orangeville holiday rentals
Among the 39 accommodations in Orangeville, here are the 4 best pet friendly rentals
8.9 193 reviews
Orangeville
21/09 – 11/12
NZ$92/nighttotal: NZ$7452 (81 )
30 Minutes Drive To Pearson Airport
1 1
apartment , Caledon
This apartment is located in Caledon, just a short drive from major stores and restaurants, offering easy access to both the town's amenities and the surrounding natural beauty. It has received very good ratings for location, cleanliness, and overall experience. This self-catering dwelling offers a comfortable space for up to two guests, with one bedroom and one bathroom. It comes equipped with amenities such as air conditioning, internet access, and parking, as well as the added benefit of being pet-friendly.
Orangeville
27/06 – 04/07
NZ$311/nighttotal: NZ$2177 (7 )
The Crown Suite
1 2
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.
Orangeville
27/06 – 04/07
NZ$398/nighttotal: NZ$2786 (7 )
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.
9.3 60 reviews
Orangeville
30/07 – 04/08
NZ$1270/nighttotal: NZ$6350 (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.
