With its scenic downtown and lively, artistic atmosphere, Orangeville is a city of captivating delights. Gorgeous panoramas, a thriving arts community, and a plentitude of outdoor recreation trails characterize this quaint Canadian town. Orangeville is steeped in picturesque charm, and is a perfect destination for a tranquil getaway. Stop in at sophisticated boutiques as you traipse along the attractive streets, and admire the brilliant carved figures on the Art Walk of Tree Sculptures that turn the downtown into an outdoor art gallery. Enjoy a plethora of outdoor adventures like paddling by the peaceful shoreline in the Island Lake Conservation Area, riding horses in the serene Mono Cliffs Provincial Park, and cycling along the Bruce Trail, Canada’s longest footpath! The nearby Alton Mill Arts Centre invites you to explore open studios and galleries, and there are excellent performances to catch at the historic Orangeville Opera House or the Theatre Orangeville. Immerse yourself in art and nature, and check out these fabulous Airbnb vacation rentals in Orangeville, Canada!
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on April 06, 2024.
1. Private hilltop cabin in Mono (from USD 160)
A spacious and elegant property, this charismatic cabin is a wonderful accommodation for a peaceful getaway. The one-bedroom house has accommodation for up to four guests and is filled with modern amenities and comfortable furnishings. With its beautiful panoramas and surrounding forest trails, the accommodation creates a tranquil atmosphere. Inside, there is a sophisticated bedroom, a cozy lounge area, a well-equipped kitchen, and a modern bathroom. This charming house is located in Mono, close to the Bruce Trail, Hockley Ski and Resort, and Mansfield Ski Club, and the hosts offer cooking and yoga classes.
Top guest reviews
Amenities & Room:
loved the stylish fan abovewe had breakfast and a three course dinner prepared by jeffery which was excellentbefore retiring we enjoyed a dip in the inground pooldefinitely take a dip in the pool and take a hike around the propertythe fireplace was so lovely and that king size bed just exceeded all expectationCleanliness:
relaxing clean and well appointedthis cabin was very clean and had everything we neededit was clean cozy and a great getawaytheir cabin was sparkling clean and in a quiet settingthe cabin was spotless and beautifully decorated / furnishedHost:
jill and jeff were amazing hostsjill and jeff were considerate accommodating and attentive hostsjill and jeff are amazing hosts quick to respond and very accommodatingjill is the perfect host -- thoughtful and very accommodatingit is worth the price and the hosts were wonderfulRead more reviewsLocation:
fantastic place away from the cityreally nice location about an hour outside of torontothe cabin is in a great location - it's easy to access yet remote enough to be very peacefulgreat cabin remote yet close to the citythe location and cabin is so lovely
Superhost
2. Private two-bedroom suite with a hot tub and a pool (from USD 61)
This gorgeous, private suite in Orangeville provides a relaxing guest experience. Filled with modern amenities, this two-bedroom suite is stylishly decorated and can accommodate up to six guests. The space and consists of two elegant bedrooms and a serene bathroom. An outdoor hot tub and pool is right outside the door, and there are plenty of walking trails that run through a nearby conservation area. This beautiful property is situated near the town center of Orangeville and is close to many art galleries, restaurants, and hiking trails.
Top guest reviews
Amenities & Room:
the thoughtful items in the kitchenette were a nice touch and the kids really enjoyed the poolwe were struck by how beautiful cozy and carefully planned her home isfantastic space spacious and comfortable the hot tub was definitely appreciatedCleanliness:
clean and cozy spacevery clean and cozyvery clean and comfortableeverything was very cleanvery clean and very welcomingHost:
she is a fabulous hostsusan was a wonderful hostsusan is a wonderful hostsusan is a wonderful hostsusan was great host quick responses and gave us our privacyRead more reviewsLocation:
great location close to shopping and parksit’s a great location as there are bike paths behind the house and easy access to storessusan’s place was great the location was ideal for a visit to orangevillegreat location walking distance to local amenitiesvery cute place and even had lots of food/drinks in the fridge
3. A charming one-bedroom carriage house (from USD 108)
This lovely one-bedroom carriage house is located in a charming rustic environment a few minutes from the ski hills. It comes with unique features like Wi-Fi, PS3, a private washroom and a gym facility. The living area is spacious and is furnished with cozy sofas, a flat-screen TV, a table, and an indoor fireplace. It comes with a fully equipped country kitchen with a fridge. The bedroom is furnished with a queen-size bed. There are two outdoor patios where guests can enjoy a barbecue.
Top guest reviews
Amenities & Room:
great amenities like a stocked breakfast bar would definitely recommendexceptional whimsical cozy romantic well stocked breakfast area great coffee tea snacksthe loft bedroom was very nice and the sofa bed was also comfortablewe had the most comfortable staythe included breakfast was much appreciated and a great selectionCleanliness:
incredibly clean and cozyspotlessly clean and a quirky interesting decorthe place was clean tidy and decorated really wellthe carriage house was very clean and comfortablethe place was clean and neat lot's of wood for the fireplaceHost:
they were great hostsbill is a wonderful hostreally lovely place with friendly staffbill and tatiana were amazing hosts from the startbill was very friendly and a excellent hostRead more reviewsLocation:
loved that the location was rural but a short drive to orangevilleit's also super close to do some shopping in orangevillegreat place to enjoy a vacation away so close to the citythe pond was a bonus walk destinationthe land and location are beautiful and an ideal short getaway from toronto
4. Spectacular cabin in the woods (from USD 121)
Marvel at the gorgeous scenery of tranquil woods when you rent this gorgeous cabin. Located in Caledon, the cabin is rustic and cozy, and provides accommodation for up to two guests. Inside the property you’ll find two comfortable beds, a compact half-bath, and a small dining table. The Victorian main house is only a few minutes away, and guests can use the kitchen and bathroom facilities here. The cabin sits in a wonderful, natural oasis! Lounge on the wooden deck outside and take in the beauty of the surrounding trees and the azure pond. The property is close to Orangeville and Hockley Valley.
Top guest reviews
Amenities & Room:
we had a great weekend at the cabin the space was cozy and relaxingCleanliness:
quiet clean and charmingHost:
the staff were amazingthe hosts are very welcoming and have provided many wonderful touches throughouteveryone including the maintenance staff and the cleaners were so friendly and accommodatingwonderful touches and friendly hostsbill and his staff are so warm and welcomingRead more reviewsLocation:
this location was perfect for our short get away from torontobills place was so cute & private perfect getawaythe cabin in the woods and house close by are very nice and a perfect getaway north of torontoit’s a perfect place to spend some time in a peaceful place and not far from torontobeautiful location and awesome hospitality
5. Two-bedroom guesthouse in a rural estate (from USD 94)
This charming cabin provides a cozy and comfortable guest experience. Filled with modern amenities, this two-bedroom guest house can accommodate up to four guests and has its own private entrance. There is a small kitchen stocked with appliances, a relaxing living area, two chic bedrooms, and a neat bathroom. A beautiful deck is the perfect place to enjoy views of the scenic gardens and lush forest, and there are two elegant gazebos to relax in. The property is surrounded by walking trails through the forest, and there are many art studios, antique stores, and restaurants nearby.
Top guest reviews
Amenities & Room:
the rooms are beautifully appointed with modern amenities amongst vintage antiqueswas beautifully decorated comfortable and the necessary staples were all in placecomfortable beds great ambiance and hassle freeone of the bedrooms is actually the living room with a sofa bed but was more than adequatethe apartment is very comfortable and the setting is stunningCleanliness:
very clean and comfortableclean quiet and well apportionedthe house is clean and is furnished beautifullythe apartment was very clean and the neighbourhood rural and quietthe cleanliness the quality and the property were amazingHost:
bill was a great hostbill was a good hostbill and kelly were amazing hostsbill & kelly were wonderful hoststhey are great hostsRead more reviewsLocation:
the location is great close to the town but also very quitegreat quiet location privacy and fresh country air close to towns (orangeville)for shoppingthe location is in a lovely wooded area it is very quiet but close to naturesuch a great location - a forest hideaway 5 minutes to orangevillethe location was wonderful peaceful and private while only 10 mins from the farthest rink
6. Treehouse cabin on an organic farm (from USD 51)
This Caledon property is a haven for vacationers looking for a rustic, eco-friendly vacation. The studio accommodation sits on an organic farm in an eco-village, and offers stunning views of the surrounding countryside. The cabin is near a beautiful pond which affords opportunities for rafting and swimming. The property is simple, and consists of a comfortable bed, with guests having access to both an outdoor shower and bathroom area, and an indoor bathroom in the main house. Up to two guests can share this space.
Top guest reviews
Amenities & Room:
loved the solar shower and showering outdoorsi loved everything about the tree house even breakfast was so goodCleanliness:
it is very clean cozythe cabin was clean and spaciousit was clean comfortable and has enough blankets to keep you warmthe space itself is a small clean room filled with sunlight and a cool breezethe cabin was clean and secluded and has electricHost:
julie was a great hostjulie is a great hostour host julie made us feel so welcomedjulie is a great host and is super welcoming :)the host was most accommodating best organic eggs everRead more reviewsLocation:
its location tucked in perfectly and privately a few minutes walk away from the main housewhole village is a wonderful placeit is a gem in the middle of great rolling landscapes and so close to torontoit was an amazing getaway from the city yet very close to downtown torontowhole village was a great place to stay
7. Enchanting cottage in Hockley Valley
Escape to this romantic cottage in the beautiful Hockley Valley! This delightful property retains its rustic charm, and provides accommodation for up to four guests. The enchanting studio has two luxurious beds, a cheerful living room, a quaint kitchen filled with convenient appliances, a modern bathroom, and a gorgeous outdoor deck. The stunning hills of Hockley Valley surround the charming cottage.
Orangeville, Ontario, Canada
3.89 km (2.5 mi) from Island Lake Conservation AreaTop guest reviews
Amenities & Room:
wi-fi signal was not strong enough to do much with but that made focusing on nature easyvery charming and cozy cottageother then the beds everything was absolutely amazingmore kitchen supplies would have been helpfulall in all we had a great staythere are so many thoughtful touches to make the stay comfortable and cozyCleanliness:
but everything was very clean and the cottage is well stocked with eveything you could possibly needwater is very salty would recommend bringing lots of clean drinking water otherwise fantasticthe cottage was clean warm and perfect for the four of usthe cottage itself is true to the photos clean with quaint detailswas clean and the hosts were very niceHost:
the host was very generous and friendlyhost was great thanks for having usthanks to our host for a lovely timebeautiful surroundings and a wonderful friendly hosthelene was so kind and very accommodatingRead more reviewsLocation:
very close to nice hiking trails and close to townlocation is perfect for hikinggreat time away to catch up with one of my close friendsgreat place and locationit was nice being close to the river
8. Charming and comfortable two-bedroom townhouse
A relaxed style and modern amenities make this apartment a delightful place to stay in Orangeville. The property is spacious and pleasant, and can provide accommodation for up to four guests. There are two bedrooms, a fully-equipped kitchen, bright, comfortable lounge filled with modern amenities, and 1.5 bathrooms. The relaxing deck is equipped with a BBQ. Located in Orangeville, this apartment is close to many walking trails and child-friendly splash pad park.
Orangeville, Ontario, Canada
5.54 km (3.5 mi) from Island Lake Conservation AreaTop guest reviews
Amenities & Room:
the air conditioning is amazingsuper nice touch were the emergency baskets in each room and in the kitchenthe beds were super comfy and the rooms were very tastefully decoratedwe were exceptionally comfortable staying at carlee’sclean comfortable with all the comforts of homeCleanliness:
clean and comfortablevery clean and comfortableit’s very clean and welcomingthe towhome was beautiful very clean and comfortableclean friendly and overall just a great place to stayHost:
amazing host and an immaculate homethe hosts were beyond wonderfulcarlee is a wonderful hostthank you to our hosts for the thoughtfulness and extras you provided us during our staythe host was incredibly thoughtful with little touches and made it feel like home away from homeRead more reviewsLocation:
it was close to everything we needed which was perfectthe location was good and it was easy to findthe location was perfect as the purpose of our trip was to visit relatives who lived nearbyquiet comfortable family orientatedlovely place to stay close to swimming pool and other events
9. Orangeville studio apartment
For a cozy stay, check into this neat studio apartment. Located within walking distance of Orangeville’s town center, this rental has a friendly ambiance and offers accommodation for up to two guests. The space consists of a spacious kitchen, a relaxing living space, a compact bathroom, and a comfortable bedroom.
1.97 km (1.3 mi) from Island Lake Conservation Area
10. Spacious farmhouse in Amaranth
Marvel at the stunning landscape of peaceful forests and lush hills from this splendid farmhouse! Located in Amaranth, the property is spacious, elegant, and surrounded by amazing panoramas. This property includes four cozy bedrooms, two bathrooms, a contemporary kitchen filled with appliances, a bright breakfast area, a cheery lounge area, and a gorgeous deck. There is also a large pool in the spacious back yard. This lovely rental can accommodate up to 10 guests.
Amaranth, Ontario, Canada
7.12 km (4.5 mi) from Island Lake Conservation Area
11. Master bedroom suite in 140-year-old Victorian house (from USD 65)
Revel in the amenities and attractions of Mono from this charming accommodation! The rental property is a private bedroom and bathroom within a 140-year-old Victorian house. Up to two guests can enjoy this private, pretty accommodation which has a large queen-sized bed, seating area, a television, a desk, and spacious bathroom. Guests also can use the kitchen, the gym, and the game room. The property is only a few minutes away from many hiking trails in the Hockey Valley, and is close to Orangeville.
Top guest reviews
Cleanliness:
the room was clean and comfortableeverything was spotless nice big private bathroomsa very quite and calming atmosphere and lovely clean roomsthe rooms are comfortable and very cleanthe property is beautiful and the room was clean and nicely furnished with everything we neededHost:
bill is a great hostthe host was really kind and seemed to be making sure everyone was getting help with extrasbill was an excellent hostbill and tatiana were excellent hoststhe host and his staff were very friendly responsive and accommodatingRead more reviewsLocation:
i highly recommend this airbnb locationthe grounds are wonderful to walkthe place was quiet with easy access to everything needed
Embrace arts and the outdoors in Orangeville
There is so much to discover in the charming town of Orangeville. With its plethora of beautiful recreation options, lively downtown area, and vibrant arts scene, Orangeville is a delightful destination. Start planning your getaway today and choose from this list of brilliant vacation rentals!
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