Find short term rentals in Orangeville at the best prices

30 available short term rental offers

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Orangeville short term rentals
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Best Short term and Weekly rentals in Orangeville

Best family friendly Orangeville Short term rentals

Among the 30 accommodations in Orangeville, here are the 4 best family friendly rentals

Tranquil Guest Suite - Orangeville
9.6 86 reviews
Orangeville
27/07 – 04/08
$296/nighttotal: $2368 (8 )

Tranquil Guest Suite

1 4
B&B , East Garafraxa
This peaceful holiday home is located in a quiet neighbourhood in East Garafraxa, close to lush greenery and a short drive from the town centre. It has consistently received excellent ratings from guests for its cleanliness, location, and overall experience.
This self-catering property can accommodate up to four guests and features a separate entrance, a private patio, and a fully equipped kitchen. Amenities include a comfortable living room, a modern bathroom, free Wi-Fi, air conditioning, on-site parking, and a spacious garden perfect for relaxing and enjoying the fresh air.
Garden Studio Apartment - Orangeville
10 199 reviews
Orangeville
05/10 – 26/10
$168/nighttotal: $3528 (21 )

Garden Studio Apartment

1 1
B&B , Orangeville
This one-bedroom garden apartment is situated in the heart of downtown Orangeville, just a short walk from Theatre Orangeville, the Farmers Market, and the Jazz & Blues Festival. The accommodation has consistently received excellent ratings for its cleanliness, location, and overall experience, making it a popular choice for travellers.
The studio apartment is perfect for a couple looking for a comfortable and convenient stay. It offers a modern kitchen, a bathroom, a living room with a smart TV, and a private patio overlooking a garden with a gas BBQ and fire pit, ideal for relaxing evenings.
Spacious Cozy 4br Orangeville Home W/deck! 10-minute Walk To Headwaters Hospital - Orangeville
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.
Little Blue Haven - Orangeville
10 11 reviews
Orangeville
30/07 – 04/08
$453/nighttotal: $2265 (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.

Best Orangeville lodging with a kitchen

Hockley Haven - Orangeville
10 166 reviews
Orangeville
15/09 – 25/09
$143/nighttotal: $1430 (10 )

Hockley Haven

1 2
apartment , Orangeville
This charming self-catering apartment is situated in a peaceful country setting on a five-acre property just a short walk from the Pollinator Garden & Island Lake Trails and a six-minute drive from Hockley Valley Resort and Adamo Estate Winery. The apartment has received excellent ratings for location, cleanliness and user experience.
The apartment is a newly renovated carriage house loft offering approximately 650 square feet of space, including a pull-out couch that can accommodate up to four guests. The apartment comes equipped with a fully fitted kitchen, a comfortable living area, a private garden and parking, as well as air conditioning and Wi-Fi.
Close To Tpc Toronto, Alton Mill & Millcroft Inn - Orangeville
10 6 reviews
Orangeville
07/08 – 10/08
$771/nighttotal: $2313 (3 )

Close To Tpc Toronto, Alton Mill & Millcroft Inn

1 6
apartment , Caledon
This Victorian-style house, located in Alton, Caledon, is a short walk from the Alton Mill Arts Centre and a 1.6km drive from the Millcroft Inn & Spa.
The four-bedroom property, sleeping eight guests, offers a fully equipped kitchen, laundry facilities, private courtyards, and is within walking distance of local cafes such as Gather Cafe and R3 Bistro.
Spacious Cozy 4br Home W/patio Deck—near Hospital! - Orangeville
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.
Walk To Downtown Orangeville | Free Parking & Game - Orangeville
10 1 review
Orangeville
01/09 – 01/12
$449/nighttotal: $40859 (91 )

Walk To Downtown Orangeville | Free Parking & Game

3 2
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.

Frequently Asked Questions about short term rentals in Orangeville

  • What kind of weather can travelers expect in Orangeville?

    Orangeville has a humid continental climate, so you can expect hot summers with average highs of around 25 degrees Celsius and cold winters with average lows of around -10 degrees Celsius. You'll want to pack for all seasons!
  • What are the best short term rentals in Orangeville?

    Among the short term rentals in Orangeville, Mono — Cabin In The Woods Experience, Rural Estate Coach House Apartment and R3 Suites In The Heart Of Alton - Frontunit are the most popular ones.

  • What are the most popular festivals and events in Orangeville?

    The Orangeville Blues & Jazz Festival is a big one, held every July, and the Orangeville Fall Fair is another popular event in September. If you're looking for something a bit different, there's the Orangeville Art Crawl, a great way to explore the local art scene.
  • What are the best short term rentals with a pool in Orangeville?

    Cedarvale Cabin In The Hockley Valley, Cottage On Camp Ground and Gorgeous - Private Mansion & Venue are the best short term rentals with a pool in Orangeville.

  • Are there any famous stadiums or sports arenas in Orangeville?

    There are no professional sports stadiums or arenas in Orangeville, but the town does have a great community centre with a large gymnasium and ice rink, where you can catch some local hockey games.
  • What are the best short term rentals with a jacuzzi in Orangeville?

  • What notable natural landmarks are near Orangeville?

    The Credit River runs right through Orangeville, so you can find some lovely walking trails along its banks. Just a short drive away, you'll find the Hockley Valley, a beautiful area with rolling hills and vineyards, perfect for a scenic drive or hike.
  • What are the best short term rentals for families and kids in Orangeville?

    The best short term rentals for families and kids in Orangeville are 2 Br Home Centrally Located In Orangeville, Beautiful Getaway In Orangeville and The Potters Cottage.

  • What part of Orangeville is ideal for finding lodging?

    The downtown core of Orangeville is a great place to find hotels and guesthouses, as it's close to the main attractions and restaurants. You can also find some charming bed and breakfasts in the surrounding neighbourhoods.

Destinations nearby

Best Orangeville lodging with laundry available

Golf & Spa Retreat W/ Jacuzzi Near Tpc Toronto - Orangeville
Orangeville
08/07 – 04/09
$268/nighttotal: $15544 (58 )

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.
Entire Private 1 Bedroom Apartment In Alton Ont. A Place To Relax, Pet Friendly - Orangeville
Orangeville
01/09 – 01/12
$196/nighttotal: $17836 (91 )

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.
Spacious Basement Guest Suite - Orangeville
9.9 110 reviews
Orangeville
05/10 – 26/10
$94/nighttotal: $1974 (21 )

Spacious Basement Guest Suite

1 1
apartment , Orangeville
This charming bed and breakfast is situated just 1 kilometre from Island Lake Conservation Area and 2 kilometres from downtown Orangeville, offering easy access to both nature and urban amenities. It has consistently received excellent ratings for location, cleanliness, and overall experience.
The accommodation features one bedroom and one bathroom, comfortably accommodating two guests. Amenities include a kitchenette with a fridge, microwave, and coffee bar, a garden, free parking, and access to laundry facilities.
Bachelor Suite With Trail-walk & Waterfront Access - Orangeville
9.6 28 reviews
Orangeville
30/07 – 04/08
$197/nighttotal: $985 (5 )

Bachelor Suite With Trail-walk & Waterfront Access

1 2
B&B , Orangeville
This private suite is situated in Orangeville's historic district, close to the town's main attractions and within walking distance of scenic trails and lakeside views. It has excellent ratings for user experience, location, and cleanliness.
The suite is ideal for couples seeking a comfortable and secluded stay. It offers a private entrance, air conditioning, internet access, a garden, and parking. Guests can also enjoy lake views, explore nearby trails, and visit the town's historical landmarks and shops.

Best Orangeville lodging with air conditioning

Ann's Cozy Private Bedroom - Orangeville
10 8 reviews
Orangeville
05/10 – 26/10
$68/nighttotal: $1428 (21 )

Ann's Cozy Private Bedroom

1 1
apartment , Orangeville
This Orangeville B&B offers a peaceful, central location, convenient for exploring the town's shops and restaurants.
The self-catering guesthouse provides one bedroom, one bathroom, sleeping up to two guests, and includes amenities such as air conditioning, parking, and internet access.
10 Acres Private Bruce Trail Cottage For 14 Guests - Orangeville
9.7 6 reviews
Orangeville
08/07 – 04/09
$1318/nighttotal: $76444 (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.
The Trails Retreat (Private Cabin) - Orangeville
9.9 340 reviews
Orangeville
30/07 – 04/08
$323/nighttotal: $1615 (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.
Konia Suite - Room A In The Elegant Home - Orangeville
10 13 reviews
Orangeville
05/10 – 26/10
$125/nighttotal: $2625 (21 )

Konia Suite - Room A In The Elegant Home

1 1
house , Orangeville
The Konia Suite is a charming bed and breakfast situated in the peaceful Winterton neighbourhood of Orangeville, just 8 kilometres from the town centre, Island Lake Conservation Area, and the Headwaters Health Care Centre. The accommodation has received excellent ratings for its location, cleanliness, and overall guest experience.
The suite offers a comfortable and welcoming space for up to two guests. It features a fully equipped kitchen with a fridge, freezer, microwave oven, and dishwasher, and guests can enjoy the convenience of air conditioning and parking. The B&B is also close to various amenities and a bus stop just two minutes away, making it easy to explore the surrounding area.
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