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.

Beautiful Getaway In Orangeville - Orangeville
10 56 reviews
Orangeville
07/30 – 08/04
$153/nighttotal: $765 (5 )

Beautiful Getaway In Orangeville

1 2
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.
Gorgeous Cozy Cottage Besides A Bustling Stream, Surrounded By Gorgeous Greenery - Orangeville
9.0 18 reviews
Orangeville
09/01 – 12/01
$134/nighttotal: $12194 (91 )

Gorgeous Cozy Cottage Besides A Bustling Stream, Surrounded By Gorgeous Greenery

1 2
cottage , Orangeville
This Orangeville riverfront cottage, a 700-square-foot (65-square-meter) rental, is located one kilometer from Hockley Valley Provincial Park and 2.2 kilometers from Hockley Valley Resort, offering easy access to outdoor recreation and Theatre Orangeville.
The one-bedroom, one-bathroom home sleeps four with a sofa bed, a kitchenette including a refrigerator and microwave, air conditioning, a terrace, a garden, parking, Wi-Fi, and barbecue grills; on-request towel service is available.
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.
Fabulous Family Retreat, 1hr From To, Sleeps 8 - Orangeville
Orangeville
08/07 – 08/10
$885/nighttotal: $2655 (3 )

Fabulous Family Retreat, 1hr From To, Sleeps 8

1 6
bungalow , Orangeville
This Orangeville bungalow is located in Ontario's Headwaters region, adjacent to Island Lake Conservation with direct access for snowshoeing and trail walks, and just 10 miles from Hockley Valley Ski Resort.
This family-friendly home accommodates 8 guests with 4 bedrooms and 3 bathrooms, featuring a fully stocked entertainer's kitchen, a dedicated playroom, a lower-level ping pong table, a summer pool, a hot tub, and a home gym.

Best Orangeville vacation rentals with parking

Hockley Valley Resort - Orangeville
8.1 1501 reviews
Orangeville
07/27 – 08/04
$328/nighttotal: $2624 (8 )

Hockley Valley Resort

1 4
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.
Island Lake Guest House - Orangeville
9.9 62 reviews
Orangeville
09/15 – 09/25
$73/nighttotal: $730 (10 )

Island Lake Guest House

1 2
house , Orangeville
This studio apartment is located in Orangeville, just a short walk from Island Lake Conservation Area and less than a kilometer from the lake, offering a peaceful escape from the city. It has received excellent ratings for cleanliness, location, and user experience.
The studio features a private patio, a full kitchen, and a bathroom with a walk-in shower, accommodating up to 3 guests. Enjoy the BBQ, cedar shower, and the family-friendly atmosphere with the owners' children and dog.
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.
Charming And Peaceful Retreat With Hot Tub - Orangeville
9.3 57 reviews
Orangeville
07/30 – 08/04
$738/nighttotal: $3690 (5 )

Charming And Peaceful Retreat With Hot Tub

1 2
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.

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.

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
09/15 – 09/25
$417/nighttotal: $4170 (10 )

Walk To Downtown Orangeville With Free Parking & Games

3 2
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.
Luxurious Farmhouse On 100 Acres- 45 Mins From North Of Gta - Orangeville
Orangeville
06/27 – 07/04
$416/nighttotal: $2912 (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.

Our Favorite Pet-Friendly Vacation Rentals in Orangeville

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

The Crown Suite - Orangeville
Orangeville
06/27 – 07/04
$181/nighttotal: $1267 (7 )

The Crown Suite

1 2
apartment , Orangeville
This private upper-level apartment is located in a central district of Orangeville, offering convenient access to local amenities.
This unit accommodates up to 3 guests and features a kitchen, air conditioning, and internet, making it ideal for couples, business travelers, and small families seeking a peaceful stay.
Stay In The Heart Of Belfountain - Orangeville
10 1 review
Orangeville
07/08 – 09/04
$230/nighttotal: $13340 (58 )

Stay In The Heart Of Belfountain

1 2
apartment , Caledon
This three-bedroom apartment in Belfountain, Caledon, is located in an 1888 heritage building, steps from local cafes and shops, and minutes from the Forks of the Credit Provincial Park and Belfountain Conservation Area.
The 3-bedroom unit, sleeping up to eight guests, features a full kitchen, air conditioning, parking, internet access, and a 15% discount at the adjacent Belfountain cafe; enjoy hiking, biking, fishing, skiing, and nearby top Ontario golf courses.
Spacious Country Home-5br Near Orangeville - Orangeville
10 8 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.
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.
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