Hockley Valley Cozy Cottage With Waterfront Access!
2 4
apartment , Orangeville
This two-bedroom flat in Mono offers private waterfront access to a river, located approximately 6.1 kilometres from Orangeville's amenities and cultural attractions, including Theatre Orangeville and the Dufferin County Museum & Archives. This property accommodates up to four guests and features a fireplace, outdoor gazebo, and is conveniently situated near outdoor recreation at Hockley Valley Resort and Mono Cliffs Provincial Park.
Orangeville
30/07 – 04/08
$2451/nighttotal: $12255 (5 )
4 Bedroom With Indoor Pool, 2 Separate Kitchen
1 4
apartment , Orangeville
This four-bedroom, seven-bathroom flat is located on a 0.4-hectare plot just 2 kilometres from Orangeville town centre, offering ample outdoor space and convenient access to local attractions. This expansive residence accommodates up to 14 guests, boasting an indoor swimming pool, jacuzzi, air conditioning, and parking, making it ideal for family gatherings and exploring the parks and amenities of Orangeville.
9.4 3 reviews
Orangeville
20/06 – 27/06
$424/nighttotal: $2968 (7 )
Fall Nordic Cottage Retreat With Hot Tub 60 Minutes From City
2 2
apartment , Caledon
This two-bedroom flat is located on an 8-acre estate in Caledon, 129 kilometres from Toronto and 13 minutes from TOC Osprey, offering proximity to Theatre Orangeville and the Great War Flying Museum. This property provides accommodation for four guests, featuring two primary bedrooms with en-suite bathrooms, a kitchen with a microwave oven and dishwasher, air conditioning, a Jacuzzi, parking, and an outdoor patio, with nearby trails and arts centres like Alton Mill Arts Centre.
Orangeville
15/09 – 25/09
$133/nighttotal: $1330 (10 )
The Cozy-inn & Out
2 2
apartment , Orangeville
This upper-level flat on Second Avenue in Orangeville offers a 2-bedroom, 1-bathroom dwelling for up to 4 guests, within 500 meters of Orangeville's shops, restaurants, Theatre Orangeville, and local parks, with easy access to Highway 10. The apartment features a full kitchen, bright interiors, comfortable bedrooms, and a recently updated bathroom, making it ideal for self-catering and exploring nearby amenities.
9.9 43 reviews
Orangeville
05/10 – 26/10
$309/nighttotal: $6489 (21 )
Orangeville 3bdrm House
3 1
apartment , Orangeville
This house is located in Orangeville, just a short walk from the town centre and the picturesque Island Lake Conservation Area. The surrounding area is peaceful and offers a range of amenities and outdoor activities. The property offers a comfortable and spacious living space for up to 6 guests. It has a fully equipped kitchen, a dining room, a living room, and 3 bedrooms. Guests can enjoy a range of amenities including free Wi-Fi, air conditioning, a garden, and parking.
10 2 reviews
Orangeville
15/09 – 25/09
$149/nighttotal: $1490 (10 )
Ballo 1-bedroom Apartment
1 2
apartment , Orangeville
This one-bedroom flat is situated a short distance from the Orangeville Broadway district, providing easy access to shops, cafés, restaurants, the Saturday Farmers Market, and the Orangeville Theatre. This self-contained accommodation offers a full kitchen, a workspace, and a private garden with a seasonal swimming pool, accommodating up to two guests.
Orangeville
30/06 – 31/08
$3791/nighttotal: $235042 (62 )
Woodlands
6 3
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.
This charming bungalow is conveniently located in downtown Orangeville, within easy walking distance of the lake conservation area, gym, cinema, shops and restaurants. The property has received excellent user ratings for its location, cleanliness and overall experience. The self-contained house has two bedrooms, sleeping up to four guests, and offers a fully equipped kitchen, a comfortable living area and a private garden. Guests can enjoy the convenience of free parking, air conditioning, and modern amenities, including a smart TV and Wi-Fi.
9.9 130 reviews
Orangeville
05/10 – 26/10
$255/nighttotal: $5355 (21 )
Century Home 3 Bed With Gas Fireplace/fenced Yard And 5 Minute Walk To Broadway
1 1
apartment , Orangeville
This family-friendly holiday home is conveniently located in the city centre of Orangeville, just under 2km from Theatre Orangeville and Island Lake Conservation Area. The property has received excellent ratings for its cleanliness, location and overall experience. This 3-bedroom house can comfortably accommodate up to 6 guests and spans 158 square metres. It features a fully equipped kitchen, a cosy fireplace, a private garden, a terrace, a spa and parking, ensuring a comfortable and enjoyable stay.
Orangeville
05/10 – 26/10
$171/nighttotal: $3591 (21 )
Cozy Basement Apartment (700 Sq Ft) With Full Kitchen
1 1
apartment , Orangeville
This newly renovated 700 sq ft basement flat is centrally located in Orangeville, offering convenient access with a 2-minute walk to the hospital and a 5-minute drive to the hockey arenas. This self-catering accommodation for two features a full kitchen, air conditioning, and complimentary driveway parking, with nearby attractions including Island Lake Conservation Area and Hockley Valley Provincial Park.
9.7 12 reviews
Orangeville
20/06 – 27/06
$219/nighttotal: $1533 (7 )
The Enchanted Cottage
1 2
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 8 reviews
Orangeville
07/08 – 10/08
$450/nighttotal: $1350 (3 )
Spacious Country Home-5br Near Orangeville
5 6
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.
Best family friendly Orangeville vacation rentals
Among the 39 accommodations in Orangeville, here are the 4 best family friendly rentals
9.9 36 reviews
Orangeville
02/07 – 05/07
$437/nighttotal: $1311 (3 )
The Potters Retreat
1 2
apartment , Caledon
This charming apartment is located in the lower level of a converted stone church in the quaint village of Alton, just a short distance from local attractions. The village of Alton is peaceful and offers a tranquil setting close to the beautiful countryside of Caledon. The apartment has two bedrooms and can comfortably accommodate four guests. The apartment is equipped with a kitchen, parking, wifi, a large smart TV and a private ceramics studio on the upper level.
Orangeville
30/07 – 04/08
$1357/nighttotal: $6785 (5 )
Fabulous Family Retreat, 1hr From To, Sleeps 8
1 4
bungalow , Orangeville
This detached house is situated in Ontario's Headwaters region, just 10 kilometres from Hockley Valley Ski Resort and a short walk to Island Lake Conservation. This family-friendly property offers accommodation for 8 guests with 4 bedrooms and 3 bathrooms, featuring a fully equipped kitchen, air conditioning, a swimming pool, hot tub, garden, and a home gym, with direct access to outdoor activities such as snowshoeing and trail walks.
10 56 reviews
Orangeville
05/10 – 26/10
$185/nighttotal: $3885 (21 )
Beautiful Getaway In Orangeville
1 1
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.
9.0 18 reviews
Orangeville
20/06 – 27/06
$221/nighttotal: $1547 (7 )
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.
Best Orangeville vacation rentals with parking
10 1 review
Orangeville
30/07 – 04/08
$1603/nighttotal: $8015 (5 )
Perfect 10 Acres Private Quiet Property For Small Events & Family Gatherings
4 4
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.
8.0 3 reviews
Orangeville
05/10 – 26/10
$303/nighttotal: $6363 (21 )
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.
Orangeville
05/10 – 26/10
$441/nighttotal: $9261 (21 )
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 1 review
Orangeville
15/09 – 25/09
$192/nighttotal: $1920 (10 )
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.
Frequently Asked Questions about vacation rentals in Orangeville
What should a first-time visitor not miss in Orangeville?
You should definitely visit the Orangeville Museum, which is a great way to learn about the town's history. Also, the unique shops and restaurants on Broadway are a must-see. And for a bit of nature, head to the scenic Island Lake Conservation Area.
What are the best Airbnb and vacation rentals in Orangeville?
Which neighborhood in Orangeville should you consider for a vacation rental?
The area around the downtown core is a great choice for a vacation rental. You'll be close to all the action, including shops, restaurants, and the Orangeville Public Library. The neighbourhood of Alder Street is also popular, with its quiet streets and proximity to the Credit River.
What are the top family-friendly attractions in Orangeville?
The Orangeville Public Library has a great children's section, the Island Lake Conservation Area offers hiking trails and a playground, and the Tony Rose Memorial Sports Centre has a swimming pool and ice rink.
What are the best vacation rentals with a pool in Orangeville?
When is the best time to book a vacation rental in Orangeville?
The best time to book a vacation rental is during the shoulder seasons, from April to May and September to October, when the weather is pleasant and the crowds are smaller.
What are the best rentals for families and kids in Orangeville?
What events or festivals should visitors check out in and around Orangeville?
The Orangeville Farmers' Market takes place every Saturday from June to October, the Orangeville Fall Fair is held in September, and the Hockley Valley Jazz Festival happens in July.
What are the best rentals or Airbnbs with a jacuzzi in Orangeville?
What are the best budget-friendly activities in Orangeville?
Take a walk along the Credit River, visit the Orangeville Public Library, or enjoy a picnic at Island Lake Conservation Area. These are all free and offer a great way to experience the town.
What are the best restaurants with local dishes in Orangeville?
The Mill Street Pub is known for its classic pub fare, while The Cornerstone Restaurant offers a more upscale dining experience with local ingredients. Both are popular choices.
What are the best walking or cycling routes in Orangeville?
The Credit River Trail offers a scenic 10km paved path for walking or cycling, while the Island Lake Conservation Area has a variety of trails for all levels of hikers and bikers.
Are there pet-friendly attractions in Orangeville?
The Island Lake Conservation Area has dog-friendly trails, and many restaurants and shops in town welcome well-behaved dogs.
What are the benefits of choosing a vacation rental in Orangeville?
Vacation rentals offer more space and privacy than a hotel, and often come with amenities like a kitchen, laundry facilities, and outdoor space. They can also be a more budget-friendly option.
What are the top sports attractions and facilities in Orangeville?
The Tony Rose Memorial Sports Centre has a swimming pool, ice rink, and fitness centre. The Orangeville Tennis Club offers courts for both indoor and outdoor play.
Destinations nearby
Best Orangeville vacation rentals with a balcony
Orangeville
07/08 – 10/08
$699/nighttotal: $2097 (3 )
Walk To Downtown Orangeville With Free Parking & Games
3 6
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
02/07 – 05/07
$732/nighttotal: $2196 (3 )
Luxurious Farmhouse On 100 Acres- 45 Mins From North Of Gta
3 2
farm , 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.
Orangeville
02/07 – 05/07
$1290/nighttotal: $3870 (3 )
Luxury 4br Stay With Swim Spa, Golf And Fireplaces
4 2
house , Caledon East
This luxury four-bedroom property is situated in Inglewood, 26 kilometres from the Mississauga Convention Centre, with other attractions within a 31 to 45 kilometre radius. This spacious 465 square metre residence accommodates up to 15 guests and features a swim spa, hot tub, golf amenity, air conditioning, a garden, free WiFi, and a fitness centre, with a fully equipped kitchen and multiple fireplaces.
9.9 157 reviews
Orangeville
05/10 – 26/10
$101/nighttotal: $2121 (21 )
A Private & Stylish Urban Studio
1 1
studio , Orangeville
This charming bed and breakfast is situated in central Orangeville, just 0.7km from Theatre Orangeville and 2.1km from Island Lake Conservation Area, offering a peaceful retreat close to local attractions. The accommodation has consistently received excellent ratings for its cleanliness, location and overall experience. This one-bedroom property, spanning 59 square metres, comfortably accommodates two guests. Enjoy a range of amenities, including a fully equipped kitchen, a private terrace, a garden, a jacuzzi, and barbecue facilities.
Best pet friendly Orangeville vacation rentals
Among the 39 accommodations in Orangeville, here are the 4 best pet friendly rentals
10 95 reviews
Orangeville
05/10 – 26/10
$226/nighttotal: $4746 (21 )
Walk To Downtown Or Conservation Area, 2 Bedroom Home . Sleeps 4. Pets Welcomed
1 1
apartment , Orangeville
This apartment is situated in Orangeville, just a short walk from the town centre, offering easy access to shops, restaurants, and entertainment. It has received excellent ratings for location, cleanliness, and overall user experience. The 139 square metre property comfortably sleeps four guests in two bedrooms and one bathroom. The apartment features a fully equipped kitchen, a private patio, a luxurious bathroom with a clawfoot bathtub, and access to a garden, spa, and parking.
9.3 57 reviews
Orangeville
30/07 – 04/08
$1070/nighttotal: $5350 (5 )
Charming And Peaceful Retreat With Hot Tub
1 4
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
20/06 – 27/06
$324/nighttotal: $2268 (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.
Orangeville
01/08 – 01/08
$308/nighttotal: $112420 (365 )
House With A Pool In Caledon
1 4
apartment , Caledon
This holiday home is located in Caledon, just a short drive from Starbucks and Hockley Valley, offering easy access to local amenities and attractions. The property sits on a half-acre plot, providing privacy and ample space for gatherings. The house has four bedrooms and one bathroom, sleeping up to ten guests. Enjoy the above-ground pool, outdoor fire pit, and ample parking, as well as a fireplace, pool table, and spacious kitchen.
