Holiday rentals in Orangeville
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Quick stats about holiday rentals in Orangeville
Total holiday rentals
Explore 60 holiday rentals in Orangeville
Nightly prices starting at
Orangeville holiday rentals start at $39 SGD per night before taxes and fees
Verified guest reviews
Over 3,550 verified reviews to help you choose
Family-friendly holiday rentals
20 properties offer extra space & child-friendly amenities
Pet-friendly holiday rentals
Find 10 rentals that welcome pets
Holiday rentals with a pool
10 properties feature pools
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Wifi availability
60 of Orangeville holiday rentals include wifi access
Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Orangeville rentals
4.7 Average rating
Orangeville stays receive an average rating of 4.7 out of 5 from guests
Top-rated holiday rentals in Orangeville
Guests agree: these stays are highly rated for location, cleanliness and more.
A bright & modern urban studio
Come & unwind...in comfort. "The Snug" is a 740 square foot studio-style unit, that is bright & modern. You will be on the basement level of the main house, with a completely separate entrance. Nice kitchen & Sleek 3 pc bathroom(with rainfall shower head and heated floors). The queen bed, with luxury-firm mattress, has built in storage for all your needs. Reliable wifi so you can work at home! A short hop from Toronto, Dufferin County has all you need for a relaxing getaway! Come & See :)
Off-grid Glamping Dome Nestled in the Woods
Welcome to our private campsite in Utopia, ON. Our family’s glamping dome is your chance to experience a unique getaway surrounded by the sights & sounds of nature. Amenities include camping essentials & some glamping perks: king size bed, bbq, fireplace, Indoor incineration toilet, soap & water, outdoor shower (summer only), kettle, cooking utensils. Nearby is Purple Hill Lavender Farms, Drysdale's Tree Farm, Tiffin Conservation Area, Nottawasaga & golf courses. Wasaga Beach is 30 min away.
The Clayhill Bunkie
Looking for a place to get away that’s semi off-grid or glamping? On The Bruce Trail and minutes from Silvercreek & Terra Cotta Cons. areas, the Credit River, the villages of Glen Williams &Terra Cotta, & Georgetown. Spend your day hiking, cycling, antique hunting, tubing, or site seeing, then order in or grab take-out and come relax by a fire. 1 basket of wood is included, adding great value. You WILL hear wildlife and farm animals here. Rural property, limited electricity, beautiful views.
Pool & Private HotTub - Headwaters Retreat
Escape to our modern-rustic queen suite, perfect for your getaway. Relax in the private hot tub right outside your door, unwind by the fireplace & enjoy Netflix & Amazon TV. This cozy retreat features a private entrance, ensuite bathroom, and a second bedroom with twin beds. Steps from scenic hiking trails, minutes from the town center, your stay is ideal for outdoor adventures, wine tours, weddings, work trips or a quiet escape away. Book now for your ultimate getaway in comfort and nature!
The Trails Retreat (Private Cabin)
Beautifully renovated 2-story private hilltop cabin for romantic getaway, family stay or friends' retreat, experience a taste of the country together. Backed by forest and trails and set away from our family home, minutes to the Bruce Trail, Hockley Ski & Golf Resort, Mansfield Ski Club and charming Orangeville. Enjoy total guest privacy & spectacular sunrises. Guests are welcome to share our heated pool in season:) Add a playful Yoga/Functional Movement class or chef's dinner to your stay!
The Bee Hive - Lower Level Raised Bungalow
Kick back and relax in this calm, stylish and super equipped space. Fully self contained and private lower apartment to our home with the hosts living above. Open plan kitchen dining living area with 1 bedroom (queen bed) and 1 shower room with 8 ft ceilings. Newly renovated, almost everything new this year ready for the 2025 season. Home from home, calm and pleasant space with all the mod cons. 50" LG Smart TV, Full sized fridge freezer, dishwasher, stove, microwave and much more - Enjoy!
Hockley Riverside Cottage • Loft and Bunkie
Needing an unforgettable escape? This cozy cottage is nestled in nature along the Nottawasaga river and has large panel doors that fully open for picture worthy views & peaceful sounds of the river. A new incredible outdoor fire-pit with hanging egg chairs. A cozy indoor wood burning fireplace along with a comfy pull out couch that has a projector above for the best movie nights. Heated floors if you aren't interested in maintaining a fire, fully equipped kitchen, Wi-fi, AC and washer/dryer.
L&S Comfy Suite
Beautiful inviting space for families as well as individuals. Brand New Fully renovated area with lots of amenities for the whole family. 2 Great size bedroom with queen size beds. Jack And Jill full washroom with an amazing shower that boast body jets. Comes with all the bells and whistles. Open concept with Living room, Dining room, Full Kitchen, Washer and Dryer, free parking, work area ideal for remote work, and lots more…. NO UNREGISTERED GUESTS ARE ALLOWED AS PER HOUSE RULES.
Luxury tiny home on peaceful country estate
Escape to Heirloom Tiny Home - where macro luxury meets a micro footprint. Nestled on 23 peaceful acres, surrounded by aspen and pine forests, just 10 minutes from the picturesque town of Elora. Wake up to serene pond views as horses and sheep graze in your view. Organic linens, artisanal soaps, and a spa-like bathroom soothe the senses. Cozy up by the indoor fire and gaze at the stars. Enjoy fine dining at the Elora Mill and Spa, enjoy popular shops or hike the Elora Gorge nearby.
Hockley Haven
Kick back and relax in this calm, stylish space. Cozy 1 bedroom carriage house loft (appx 650 sq ft) above detached 3 bay garage in serene country setting on 5 acres of pine and cedar with a river running thru it. Pullout couch can accommodate 2 additional people. Walk across the road to Pollinator Garden & Island Lake Trails. 6 min drive to Hockley Valley Resort and Adamo Estate Winery, as well as beautiful downtown Orangeville boasting fabulous restaurants and quaint shops.
Stylish 3 Bedroom Getaway in Orangeville
Nestled among tree sculptures and lakes, just steps away from downtown and minutes from the serene beauty of Island Lake Conservation Area. Our urban oasis is complete with a comfortable bed, fully equipped kitchen, chic living area, and private balconies. Be transported through time as you wander the streets of downtown, admiring vintage architecture and vibrant culture. Experience the magic of nature and city living combined in one unforgettable stay!
Garden Studio Apartment
Enjoy a stylish experience at this centrally located place. Newly renovated 1 bdrm walkout apartment located in our home in downtown Orangeville. Steps to Theatre Orangeville, Orangeville farmers market, and Jazz & Blues Festival. Enjoy evenings on your own patio in a private backyard overlooking the garden. Enjoy walks on the Island lake Conservation Park.. Dine at any of the many fine restaurants or cook at meal in your own fully equipped kitchen.
Popular amenities for Orangeville holiday rentals
Stay near Orangeville's top sights
Other great holiday rentals in Orangeville
Modern Guest Apartment near downtown Orangeville.
Mono Countryside Home & Farm
Fern Hill Cabin
Little blue haven
Mono Forest Stay & Event Space
Beautiful Getaway in Orangeville
Ballo - GuestHouse
8 Acre Retreat | 5 min to Canadian Open Hot Tub!
When is the best time to visit Orangeville?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $107 SGD | $112 SGD | $118 SGD | $118 SGD | $125 SGD | $123 SGD | $127 SGD | $123 SGD | $111 SGD | $114 SGD | $115 SGD | $116 SGD |
| Avg. temp | -7°C | -6°C | -1°C | 6°C | 12°C | 17°C | 20°C | 19°C | 15°C | 9°C | 3°C | -3°C |
Frequently Asked Questions
What are the best places to stay in Orangeville?
Many guests find stays around downtown Orangeville appealing for walkable access to shops, dining, and galleries. The area near Island Lake and tree-lined neighborhoods also has a range of vacation rental options.
What are the best things to do in Orangeville with kids?
Families can explore splash pads, playgrounds, and creative workshops around Orangeville. Island Lake Conservation Area also has child-friendly trails and picnic spots, while some theaters host kid-oriented performances.
What are some of the best things to do in Orangeville?
Explore main street’s shops and tree carvings, spend time at local art galleries, or catch a live show at Theatre Orangeville. Nature seekers often walk the trails at Island Lake Conservation Area or nearby parks.
How is the weather in Orangeville?
Orangeville has cold winters, with temperatures ranging from about 12–32°F (-11–0°C), and mild autumns around 49–70°F (10–21°C). Showers or snow are common, so layering and a waterproof jacket are helpful.
When is the best time to visit Orangeville?
Late spring through early fall is often recommended for comfortable temperatures, outdoor events, and colorful landscapes. Autumn brings vibrant foliage, while summer is lively with markets and arts festivals.
What are the best places to visit in Orangeville?
Many visitors explore the tree sculpture walk downtown, the Orangeville Farmers’ Market, and Island Lake Conservation Area. Theatre Orangeville is often highlighted for its performances in a historic town hall setting.
What are some hiking trails in Orangeville?
Orangeville has a mix of forested walking paths and waterfront trails. Island Lake Conservation Area is frequently suggested for its scenic loops and accessible routes, while Mono Cliffs Provincial Park is also popular for varied terrain.
What are some family activities we can do in Orangeville?
Families often visit splash pads, community parks, or the outdoor spaces at Island Lake Conservation Area. Downtown Orangeville sometimes hosts family-friendly festivals and public art tours.
What are some of the best day trip ideas from Orangeville?
Consider exploring nearby conservation areas, touring local wineries, or discovering small towns with historic charm. Outdoor lovers often venture to Mono Cliffs Provincial Park or the Credit Valley for hiking and nature experiences.
Are there any pet friendly accommodations available in Orangeville?
Pet-friendly accommodations can be found in several Orangeville neighborhoods, especially close to parks and walking trails. Hosts in the area often welcome guests with dogs, making it easy to explore outdoor spaces together.
What are some local tips for visiting Orangeville?
Locals suggest exploring the public art, visiting weekend farmers markets, and trying seasonal treats at downtown bakeries. Autumn foliage and spring blooms bring extra color to nearby parks and trails.
What is Orangeville known for?
Orangeville is known for its lively arts scene, locally rooted markets, and the scenic Headwaters region. Visitors frequently explore its tree sculptures, historic main street, and a range of natural retreats nearby.
What are the best hidden gems to explore in Orangeville?
Discover Orangeville’s unique tree sculptures along the main streets, peek into boutique art galleries, or stroll through quiet garden spaces. Local hiking trails also reveal less-traveled corners of nearby woodlands.
What are the best foods to try in Orangeville?
Locally grown produce, artisanal cheeses, and craft baked goods are frequently suggested in Orangeville. Many visitors enjoy seasonal fare at farmers markets, along with classic Canadian dishes in the town’s cafes and restaurants.
What should I bring for a trip to Orangeville?
Pack layers to adapt to cooler mornings and warmer afternoons, especially outside summer. Comfortable shoes are helpful for exploring local shops, trails, or festivals, and a light rain jacket is often useful throughout the year.
What is the nightlife in Orangeville like?
Orangeville’s nightlife centers around relaxed pubs, local live music, and casual eateries, especially near the main street district. Occasional performances at Theatre Orangeville or neighboring music venues bring in a creative crowd.
What are the most popular events or festivals in Orangeville?
The Orangeville Blues and Jazz Festival energizes the town in early summer, while theater events, farmers markets, and seasonal fairs bring together locals and visitors year-round. Arts and busker festivals are also frequently suggested.
Are there family friendly vacation rentals in Orangeville?
Orangeville has a variety of family friendly vacation rentals, especially in its residential neighborhoods and near parks. Many homes provide spacious layouts for groups or families seeking a comfortable stay.
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- Rogers Centre
- CN Tower
- Blue Mountain Village
- Scotiabank Arena
- University of Toronto
- Union Station
- Metro Toronto Convention Centre
- Downsview Park
- The Danforth Music Hall
- Harbourfront Centre
- Toronto Eaton Centre
- Toronto Zoo
- Scarborough Town Center
- Exhibition Place
- Nike Square One Shopping Centre
- Trinity Bellwoods Park
- Casa Loma
- Snow Valley Ski Resort
- Yorkdale Shopping Centre
- Massey Hall
- Enercare Centre
- Elora Gorge
- York University
- Beaver Valley Ski Club