Vacation rentals in Orangeville

39 available vacation rental offers

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Orangeville vacation rentals
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Best Vacation rentals and Airbnb offers in Orangeville

Top Vacation Rentals for Families in Orangeville

The right family vacation rental in Orangeville makes all the difference, keeping you close to top city attractions.

Walk To Downtown Orangeville | Free Parking & Game - Orangeville
10 1 review
Orangeville
09/01 – 12/31
$321/nighttotal: $38841 (121 )

Walk To Downtown Orangeville | Free Parking & Game

3 1
apartment , Orangeville
This Orangeville apartment is located in a tranquil district, offering a peaceful escape and convenient access to local landmarks.
This rental property accommodates up to six guests and features two bathrooms, a kitchen, air conditioning, and internet, providing a quiet retreat with proximity to Orangeville's attractions.
Beautiful Getaway In Orangeville - Orangeville
9.9 57 reviews
Orangeville
07/27 – 08/04
$190/nighttotal: $1520 (8 )

Beautiful Getaway In Orangeville

1 4
apartment , Orangeville
This apartment in Orangeville offers an excellent location and amenities for travelers. It's family-friendly and has a garden, parking, and air conditioning. The kitchen is equipped with a fridge and freezer, and there's also internet access.
With a user rating of excellent, this one-bathroom apartment can accommodate up to four guests. It's a great choice for those looking for a comfortable and convenient stay in Orangeville.
Spacious Country Home-5br Near Orangeville - Orangeville
9.3 12 reviews
Orangeville
07/27 – 08/04
$276/nighttotal: $2208 (8 )

Spacious Country Home-5br Near Orangeville

5 4
gîte , Amaranth
This five-bedroom Amaranth house, ideal for large groups, offers ample parking and a detached 24' x 24' garage/workshop.
The 1-acre property features an open-concept living area, fully equipped kitchen, gas fireplace, flat-screen TV, high-speed Wi-Fi, and accommodates up to ten guests.
Spacious Cozy 4br Home W/patio Deck—near Hospital! - Orangeville
8.0 3 reviews
Orangeville
10/05 – 10/26
$216/nighttotal: $4536 (21 )

Spacious Cozy 4br Home W/patio Deck—near Hospital!

4 1
apartment , Orangeville
This four-bedroom rental home is situated in Orangeville, offering a 10-minute walk to Headwaters Health Care Centre and a 5-minute drive to Mount Alverno Luxury Resorts, with proximity to Island Lake Conservation Area and Broadway boutiques.
This fully furnished residence accommodates up to 10 guests and features air conditioning, a full kitchen with a dishwasher, two bathrooms with jacuzzis, a garden, a fitness center, parking, and an outdoor patio with a BBQ, all supported by complimentary fast, free Wi-Fi.

Best Orangeville vacation rentals with parking

Hockley Valley Resort - Orangeville
8.1 1501 reviews
Orangeville
06/27 – 07/04
$392/nighttotal: $2744 (7 )

Hockley Valley Resort

1 2
resort , Orangeville
The Hockley Valley Resort is a family-friendly lodging option located in Orangeville, less than a 15-minute drive from Hockley Valley Provincial Nature Reserve and Orangeville itself.
This resort offers an 8,000 sq. foot spa, year-round recreational facilities including indoor and outdoor pools, an 18-hole golf course, a ski hill, and three dining options, with spacious rooms featuring modern amenities and free Wi-Fi.
Luxurious Farmhouse On 100 Acres- 45 Mins From North Of Gta - Orangeville
Orangeville
06/27 – 07/04
$425/nighttotal: $2975 (7 )

Luxurious Farmhouse On 100 Acres- 45 Mins From North Of Gta

3 2
farm , Amaranth
This Amaranth farm rental, a 12-minute drive from Mono Cliffs Provincial Park and 17 minutes from Island Lake Conservation Area, offers convenient access to outdoor recreation.
This 4,305-square-foot vacation home boasts four bedrooms, three bathrooms, sleeps ten guests, and includes amenities such as a full kitchen, tennis court, and Wi-Fi—perfect for family gatherings near Shelburne Golf & Country Club.
A Bright & Modern Urban Studio - Orangeville
9.9 97 reviews
Orangeville
10/05 – 10/26
$85/nighttotal: $1785 (21 )

A Bright & Modern Urban Studio

1 1
apartment , Orangeville
This Orangeville basement studio apartment is located in Dufferin County, a short drive from Toronto, offering a peaceful escape in the countryside.
This 740-square-foot (approximately 69 square meters) unit features a private entrance, one bedroom, one bathroom, a full kitchen with dishwasher, a private patio with propane BBQ, fast internet, and parking; it comfortably sleeps two guests.
A Modern 3 Bedroom Home With Free Parking & Wifi - Orangeville
9.7 131 reviews
Orangeville
10/05 – 10/26
$123/nighttotal: $2583 (21 )

A Modern 3 Bedroom Home With Free Parking & Wifi

1 1
apartment , Orangeville
This Orangeville home is located in a quiet residential area, just a 15-minute walk from the downtown core and its shops and restaurants. The home has received excellent ratings for location, cleanliness, and overall experience from previous guests.
This 3-bedroom, 2-bathroom home comfortably sleeps up to five guests. The home has a fully equipped kitchen, a spacious backyard, and free Wi-Fi, plus parking for two vehicles.

Frequently Asked Questions about vacation rentals in Orangeville

  • What should a first-time visitor not miss in Orangeville?

    You'll definitely want to check out the unique shops and restaurants on Broadway, the main street in Orangeville. You should also visit the Orangeville Museum, which showcases the town's history. And if you are looking for a beautiful outdoor experience, head to the Island Lake Conservation Area.
  • What are the best Airbnb and vacation rentals in Orangeville?

    Mono - Charming - Rustic 150 Year Carriage House, Rural Estate Coach House Apartment and R3 Suites In The Heart Of Alton - Frontunit are the most popular Airbnb and vacation rentals in Orangeville among travelers.

  • Which neighborhood in Orangeville should you consider for a vacation rental?

    The downtown area, close to Broadway, is a great choice. It's walkable to many restaurants, shops, and attractions. If you're looking for a quieter stay, consider the neighborhoods around Island Lake, which offers a peaceful lakefront setting.
  • What are the most popular Airbnbs in Orangeville?

  • What are the top family-friendly attractions in Orangeville?

    The Island Lake Conservation Area is a great place for families, with hiking trails, a playground, and a beach. The Orangeville Public Library is also a great spot for kids, with regular story times and events. And if you're visiting in the summer, the Orangeville Farmers Market is a fun way to spend a morning.
  • What are the best vacation rentals with a pool in Orangeville?

  • When is the best time to book a vacation rental in Orangeville?

    Booking a vacation rental in Orangeville during the shoulder seasons, like spring or fall, can often get you better deals and avoid the crowds. You'll still have pleasant weather for outdoor activities, and the town is less busy.
  • 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 Agricultural Society hosts the Orangeville Fair in August, which features live music, agricultural exhibits, and a midway. The town also hosts a variety of events throughout the year, including the Orangeville Ribfest in July, so check the town's website for a complete calendar.
  • What are the best rentals or Airbnbs with a jacuzzi in Orangeville?

  • What are the best budget-friendly activities in Orangeville?

    The Orangeville Farmers Market is a great way to experience local produce and crafts for a low cost. You can also enjoy a picnic at Island Lake Conservation Area, where you can hike the trails and enjoy the scenery for free. And if you're looking for a fun, free activity, check out the Orangeville Public Library's events calendar.
  • What are the best restaurants with local dishes in Orangeville?

    The Mill Street Grill is a popular spot for local favorites, with dishes like their signature burgers and fish and chips. The Cornerstone Pub & Grill also offers a great selection of classic pub fare. For a more upscale dining experience, try the restaurant at the Hockley Valley Resort.
  • What are the best walking or cycling routes in Orangeville?

    The Island Lake Conservation Area has a network of trails for both walking and cycling. You can also enjoy a scenic ride along the Credit River Trail, which runs through Orangeville and beyond.
  • Are there pet-friendly attractions in Orangeville?

    The Island Lake Conservation Area is pet-friendly, allowing dogs on leash on the trails and in designated areas. You can also enjoy a walk with your furry friend along the Credit River Trail.
  • 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 kitchens and laundry facilities. They can also be a more affordable option, especially for families or groups.
  • What are the top sports attractions and facilities in Orangeville?

    Orangeville is home to the Orangeville Hawks, a junior hockey team in the Ontario Junior Hockey League. The town also has a number of recreational facilities, including the Orangeville Tennis Club and the Orangeville Golf Club.

Destinations nearby

Best Vacation Rentals with Balconies in Orangeville

Enjoy your own private terrace with city skyline views at these vacation rentals in Orangeville.

Walk To Downtown Or Conservation Area, 2 Bedroom Home . Sleeps 4. Pets Welcomed - Orangeville
10 95 reviews
Orangeville
10/05 – 10/26
$172/nighttotal: $3612 (21 )

Walk To Downtown Or Conservation Area, 2 Bedroom Home . Sleeps 4. Pets Welcomed

2 1
apartment , Orangeville
This Orangeville apartment is located within walking distance of the downtown area, offering easy access to shops, restaurants, and attractions. It has excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The 1,500 square foot unit comfortably accommodates four guests with two bedrooms and one bathroom. It features a private patio, a jacuzzi, a spa, a garden, and parking, providing a relaxing and convenient stay.
Scenic Casa Azul Retreat With Jacuzzi & Gazebo - Orangeville
Orangeville
06/27 – 07/04
$226/nighttotal: $1582 (7 )

Scenic Casa Azul Retreat With Jacuzzi & Gazebo

3 2
apartment , Caledon
This Caledon rental, a countryside retreat in Alton, offers 2400 sq ft of living space with three bedrooms and two bathrooms for up to six guests, featuring a dedicated workspace and ample parking. Enjoy outdoor amenities like a deck, gazebo, and jacuzzi, with convenient access to Highway 10, placing you a short drive from Orangeville's shops and restaurants, and close to Forks of the Credit Provincial Park, Belfountain Conservation Area, Cheltenham Badlands, and Island Lake Conservation Area.
A Private & Stylish Urban Studio - Orangeville
9.9 157 reviews
Orangeville
10/05 – 10/26
$72/nighttotal: $1512 (21 )

A Private & Stylish Urban Studio

1 1
studio , Orangeville
This charming bed and breakfast is conveniently located in Orangeville, just a short walk from Theatre Orangeville and Island Lake Conservation Area. Guests consistently praise the bed and breakfast for its excellent location, cleanliness, and overall experience.
The cozy guesthouse features a spacious bedroom and bathroom, perfect for couples seeking a relaxing getaway. Guests can enjoy a variety of amenities, including a private terrace, a well-equipped kitchen, and a relaxing jacuzzi.
Walk To Downtown Orangeville With Free Parking & Games - Orangeville
Orangeville
10/05 – 10/26
$383/nighttotal: $8043 (21 )

Walk To Downtown Orangeville With Free Parking & Games

3 1
house , Orangeville
This Orangeville vacation home offers prime walkability to Downtown Orangeville, placing guests within a 7-minute walk of Theatre Orangeville and between 28 to 31 miles from Mississauga Convention Center, Apollo Convention Centre, and Toronto Pearson International Airport.
This air-conditioned, 3-bedroom, 3-bathroom rental accommodates up to 11 guests with a fully equipped kitchen, fireplace, balcony, and an on-site indoor play area, with complimentary parking and Wi-Fi provided.

Our Favorite Pet-Friendly Vacation Rentals in Orangeville

Discover pet-friendly vacation rentals in Orangeville that prioritize comfort for both you and your dog.

10 Acres Private Bruce Trail Cottage For 14 Guests - Orangeville
9.7 6 reviews
Orangeville
07/08 – 09/04
$943/nighttotal: $54694 (58 )

10 Acres Private Bruce Trail Cottage For 14 Guests

1 2
apartment , Caledon
This Caledon cottage, located on 10 acres bordering the Bruce Trail and 45 minutes from Yorkdale Shopping Centre, offers direct access to hiking trails and stunning Niagara Escarpment views.
The 3,700-square-foot home features four bedrooms, three bathrooms, sleeping up to 14 guests, a fully equipped kitchen with dishwasher, and a solarium perfect for yoga; enjoy the private creek on the property and ample parking.
Ballo 2-bedroom Apartment - Orangeville
9.4 7 reviews
Orangeville
09/21 – 12/11
$83/nighttotal: $6723 (81 )

Ballo 2-bedroom Apartment

2 1
apartment , Orangeville
This Orangeville dwelling offers a lower unit with private backyard access, situated minutes from Broadway's shops, cafes, restaurants, the Saturday Farmers Market, and the historic Opera House.
This 2-bedroom, 1-bathroom condo accommodates up to 5 guests and features a seasonal swimming pool, dedicated workspace, full kitchen, and in-unit laundry, making it ideal for families or remote workers seeking convenience and comfort.
Charming And Peaceful Retreat With Hot Tub - Orangeville
9.3 57 reviews
Orangeville
07/27 – 08/04
$604/nighttotal: $4832 (8 )

Charming And Peaceful Retreat With Hot Tub

1 4
apartment , Caledon
This Caledon house rental, located in a peaceful neighborhood, is minutes from TPC Toronto at Osprey Valley, Hockley Valley Resort, and Caledon Ski Club.
The 6-bedroom, 3-bathroom home sleeps 12, features a fully equipped kitchen with a wine fridge, a hot tub, and a large deck with a BBQ, perfect for family gatherings or group getaways.
House With A Pool In Caledon - Orangeville
Orangeville
08/01 – 08/01
$220/nighttotal: $80300 (365 )

House With A Pool In Caledon

1 4
apartment , Caledon
Escape to tranquility at this charming accommodation nestled amidst the picturesque Hockley Valley of Caledon. Just minutes from Starbucks and Hockley Valley Provincial Park, this retreat offers a serene and convenient base for exploring the region's natural beauty and amenities.
Accommodating up to 10 guests in its 4 bedrooms, this property features an array of amenities, including an above-ground pool, outdoor fire pit, pool table, and stylish washrooms. Ample parking and free Wi-Fi ensure a hassle-free stay, while the spacious property and flexible event space make it ideal for family gatherings and special occasions.
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