Best Vacation Homes in Dufferin County
Cabin
10.0(97 Reviews)
1 Bedroom
1 Bath
4 Guests
950 ft²
Skiing
Fireplace/Heating
Balcony/Terrace
Pet Friendly
US $217/Night
7 Nights - US $1,519
House
10.0(1 Review)
3 Bedrooms
3 Baths
6 Guests
10.76 ft²
- Fireplace/Heating
- Pet Friendly
Internet
Child Friendly
US $455/Night
7 Nights - US $3,188
Cabin
8.2(23 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
Breakfast
Parking
US $71/Night
7 Nights - US $497
Apartment
10.0(45 Reviews)
1 Bedroom
1 Bath
2 Guests
300 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
Kitchen
US $138/Night
7 Nights - US $964
Bed & Breakfast
9.8(67 Reviews)
3 Bedrooms
3 Baths
6 Guests
387.5 ft²
Oceanfront
Spa- Skiing
- Fireplace/Heating
US $154/Night
7 Nights - US $1,078
Apartment
10.0(15 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $102/Night
7 Nights - US $714
House
10.0(12 Reviews)
2 Bedrooms
1 Bath
4 Guests
1500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $196/Night
7 Nights - US $1,373
House
10.0(12 Reviews)
1 Bedroom
1 Bath
2 Guests
634 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $102/Night
7 Nights - US $713
Dufferin County Luxury Rentals
House
5 Bedrooms
5 Baths
12 Guests
4750 ft²
Private Pool- Spa
- Fireplace/Heating
Pool
US $2,416/Night
7 Nights - US $16,913
Cottage
10.0(2 Reviews)
4 Bedrooms
3 Baths
10 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $1,177/Night
7 Nights - US $8,236
House
4.0(1 Review)
4 Bedrooms
2 Baths
12 Guests
- Fireplace/Heating
- Kitchen
- Parking
Air Conditioner
US $1,023/Night
7 Nights - US $7,158
House
10.0(49 Reviews)
5 Bedrooms
2 Baths
10 Guests
4600 ft²
- Private Pool
Hot Tub- Skiing
- Fireplace/Heating
US $1,015/Night
7 Nights - US $7,105
House
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $1,001/Night
7 Nights - US $7,009
New
House
5 Bedrooms
3 Baths
10 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $889/Night
7 Nights - US $6,222
New
House
10.0(5 Reviews)
7 Bedrooms
2 Baths
10 Guests
3750 ft²
- Skiing
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $814/Night
7 Nights - US $5,696
New
Other
4 Bedrooms
3 Baths
10 Guests
2000 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $471/Night
7 Nights - US $3,300
Dufferin County Pet Friendly Vacation Rentals
Cottage
8.8(19 Reviews)
1 Bedroom
1 Bath
4 Guests
700 ft²
- Fireplace/Heating
Ocean View- Balcony/Terrace
View
US $181/Night
7 Nights - US $1,268
House
7.0(1 Review)
1 Bedroom
1 Bath
2 Guests
1001.04 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- View
US $197/Night
7 Nights - US $1,379
Hotel
8.8(245 Reviews)
1 Bath
- Pool
- Breakfast
- Pet Friendly
- Parking
US $168/Night
7 Nights - US $1,174
Apartment
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $150/Night
7 Nights - US $1,048
Apartment
3 Bedrooms
2 Baths
7 Guests
1485.42 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Pet Friendly
US $194/Night
7 Nights - US $1,357
House
10.0(20 Reviews)
3 Bedrooms
1 Bath
6 Guests
1700 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $230/Night
7 Nights - US $1,612
House
9.4(3 Reviews)
4 Bedrooms
3 Baths
9 Guests
2400 ft²
- Private Pool
- Skiing
- Fireplace/Heating
- Pool
US $470/Night
7 Nights - US $3,288
New
Apartment
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $143/Night
7 Nights - US $1,004
Dufferin County Large Vacation Homes
House
10.0(4 Reviews)
9 Bedrooms
4 Baths
16 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $1,824/Night
7 Nights - US $12,770
House
8.5(2 Reviews)
5 Bedrooms
3 Baths
10 Guests
3799.66 ft²
- Fireplace/Heating
- View
- Air Conditioner
- Internet
US $449/Night
7 Nights - US $3,143
House
10.0(3 Reviews)
6 Bedrooms
5 Baths
14 Guests
- Hot Tub
- Spa
- Fireplace/Heating
- Balcony/Terrace
US $1,596/Night
7 Nights - US $11,169
House
7.5(2 Reviews)
4 Bedrooms
3 Baths
10 Guests
2970.84 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $390/Night
7 Nights - US $2,733
House
10.0(1 Review)
5 Bedrooms
2 Baths
10 Guests
4400 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $444/Night
7 Nights - US $3,105
House
8.0(5 Reviews)
4 Bedrooms
1 Bath
11 Guests
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $240/Night
7 Nights - US $1,677
Ski Chalet
8.0(1 Review)
5 Bedrooms
5 Baths
12 Guests
- Spa
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $1,459/Night
7 Nights - US $10,216
House
8.0(1 Review)
5 Bedrooms
3 Baths
10 Guests
3800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $418/Night
7 Nights - US $2,927
Why Choose Rent By Owner for your Dufferin County Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Dufferin County
When should you plan your Vacation Rentals stay?
Choosing the right time to vacation here can enhance your experience, allowing you to enjoy the region’s natural beauty and local charm at its best, whether you're seeking outdoor adventures or tranquil relaxation.
Peak Season Highlights
Summer (June to August)
During the warm summer months, you can enjoy the scenic beauty and outdoor activities in this region, making it an ideal time for a relaxing getaway.
Average Temperature Daytime: 25°C to 28°C - Nighttime: 15°C to 18°C
Fall (September to November)
In early fall, the area features vibrant foliage that enhances your stay, providing perfect conditions for outdoor exploration and photography.
Average Temperature Daytime: 15°C to 20°C - Nighttime: 8°C to 12°C
Off-Season Highlights
Spring (March to May)
As spring arrives, the region begins to blossom, offering a quieter atmosphere for those seeking tranquility in their vacation rentals.
Average Temperature Daytime: 10°C to 15°C - Nighttime: 3°C to 7°C
Winter (December to February)
During winter, the area provides a peaceful setting for enjoying cozy accommodations and winter landscapes, ideal for a quiet retreat.
Average Temperature Daytime: -5°C to 0°C - Nighttime: -10°C to -4°C
Weekly Weather Forecast for Dufferin County
How to Book Your Dufferin County Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Dufferin County
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor dining with a private BBQ grill, perfect for summer evenings in the region.
- Relax by a cozy fire pit, ideal for making memories under the starry night sky.
- Take advantage of spacious yards or gardens for outdoor activities and family fun.
- Experience privacy and tranquility in outdoor spaces surrounded by natural scenery.
- Benefit from access to shared or private swimming pools when staying at select properties nearby.
- Use outdoor sports equipment such as volleyball nets or badminton sets for active entertainment.
- Explore walking trails or picturesque landscapes directly from your rental’s outdoor area.
Top Attractions Around Dufferin County
What attractions are nearby?
While staying in this destination, you can enjoy a variety of outdoor activities and cultural experiences just moments from your vacation rentals, making it an ideal spot to explore the natural beauty and local charm of the region.
Family Activities
- Sherwood Park Area: Enjoy an outdoor adventure by exploring the scenic trails and playgrounds perfect for family outings in this natural setting.
- Dufferin County Museum & Archives: Discover local history through engaging exhibits and activities that captivate children and adults alike in this educational attraction.
- Island Lake Conservation Area: Spend a day kayaking, fishing, or picnic overlooking serene waters, offering a peaceful retreat for families seeking outdoor fun.
- Downey’s Farm Market & Adventure Park: Experience farm life with seasonal activities, hayrides, and petting farms designed to entertain and educate children during your visit here.
Adult Activities
- Visit Orangeville's Art Scene: Explore local galleries and studios to immerse yourself in the vibrant creative community that thrives within this charming area.
- Enjoy Outdoor Adventures at Island Lake Conservation Area: Take advantage of scenic hiking trails, tranquil fishing spots, and peaceful picnicking areas perfect for a relaxing day outdoors.
- Discover Local Wineries and Breweries: Sample regional wines and craft beers at nearby establishments, offering a taste of the region's growing artisanal scene.
- Experience Cultural Events at the Dufferin County Museum & Archives: Delve into the area's history through engaging exhibits and special programs designed for visitors seeking a cultural connection.
Other Places to Stay in Dufferin County, ON
Luther Marsh Conservation Area
East Garafraxa
Dufferin County Museum & Archives
Amaranth
Dunadel Golf
Melancthon
Hockley Valley Resort
Mulmur
Orangeville
Mansfield
Shelburne
Dufferin County Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Events and Activities: Check the area’s community calendar to discover festivals, outdoor activities, and cultural events during your stay, ensuring you experience the region's vibrant local scene.
- Choose Strategic Accommodation Locations: Opt for vacation rentals near key attractions or access points to make exploring this destination more convenient and enjoyable.
- Plan Outdoor Adventures: Take advantage of the region’s natural beauty by scheduling hikes, nature walks, or outdoor sports that highlight the area's scenic landscapes.
- Connect with Local Cuisine: Visit local eateries or prepare meals in your rental to enjoy authentic regional flavors and get a true taste of this destination’s culinary offerings.
Transportation Options
- Personal Vehicle: Renting or using your own car offers the most flexibility to explore Dufferin County and its scenic surroundings at your own pace.
- Local Bus Service: The area is served by regional bus routes that connect key towns and parks, making it convenient for travelers without a vehicle.
- Taxi and Ride-Sharing Services: Taxis and ride-sharing options like Uber provide quick, reliable transportation within Dufferin County and nearby attractions.
- Rental Cars: Booking a rental car here allows you to comfortably navigate the region's rural landscapes and access remote vacation rentals with ease.
Local Customs Options
- Seasonal Harvest Celebrations: You can participate in local harvest festivals that celebrate the region's agricultural heritage each fall, providing a glimpse into traditional farming customs.
- Community Potlucks and Gatherings: Engaging in community potlucks offers an authentic way to experience local hospitality and share in regional culinary traditions.
- Historic Trail Etiquette: When exploring here’s historic sites and trails, it’s customary to show respect by staying on designated paths and honoring local preservation efforts.
- Farmer’s Market Traditions: Visiting farmers markets allows you to embrace the region’s emphasis on fresh, locally sourced products while supporting local producers.
Dufferin County Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Dufferin County?
There are a lot of options in Dufferin County. If you plan on staying in the Dufferin County area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Dufferin County:
- Molly's Retreat B and B
- A charming, rustic 150 year old Carriage House
- Foxingham Farm Bed & Breakfast
- A rustic cabin in the woods
- Hampton Inn & Suites Orangeville, On
- 5BR Riverfront Retreat w Firetable BBQ and Deck
- Best Western Plus Orangeville Inn & Suites
- Hockley Valley Resort
- Spacious 4 Bedroom Home in Orangeville with Free Parking, Laundry & Private Deck - 10 Min Walk to Headwaters Hospital, 5 Mins to Mount Alverno - Great for Medical & Family Stays!
- Atlanta Motel
2. How many vacation rentals have private pools in Dufferin County?
There are 4 vacation rentals with private pools near Dufferin County. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Dufferin County are best for families?
If you are looking for a family-friendly vacation home in Dufferin County, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Dufferin County:
4. How many Rentbyowner vacation rentals are available in Dufferin County?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 149 in the Dufferin County area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Dufferin County.
5. What is the cancellation policy for vacation rentals in Dufferin County, Ontario?
Cancellation policies vary by listing. You should review the specific rental's cancellation terms on the booking page or contact the property owner directly to understand the options and any applicable fees.
6. How do I ensure my booking is secure when reserving a vacation rental in the area?
Bookings are protected through secure payment methods and verified listings. It’s recommended to confirm details with the host and use the platform’s messaging system to communicate before confirming your reservation.
7. Are there any additional fees or charges for staying in a vacation rental here?
Additional fees such as cleaning, service charges, or local taxes may apply. These details are specified in the listing description and final invoice, so reviewing them beforehand helps avoid surprises.
8. What amenities can I expect from vacation rentals in this destination?
Amenities vary by property but typically include essentials like Wi-Fi, parking, and kitchen facilities. Check each listing for specific amenities to ensure they meet your travel needs.
9. How do I find the best vacation rental options in this region that suit my budget?
Filtering search results by price range, guest ratings, and specific amenities will help you find options that match your budget and preferences. Reading reviews and contacting hosts directly can also provide helpful insights.
Dufferin County Top Rated Vacation Rentals
Hotel
8.8(962 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Breakfast
- Kitchen
US $197/Night
7 Nights - US $1,379
Hotel
8.5(168 Reviews)
1 Bath
- Private Pool
- Pool
- Pet Friendly
- Parking
US $224/Night
7 Nights - US $1,565
US $267/Night
7 Nights - US $1,871
Resort
7.8(434 Reviews)
7 Baths
22 Guests
534.61 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Spa
US $297/Night
7 Nights - US $2,078
Ski Chalet
2 Bedrooms
2 Baths
4 Guests
107.64 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $348/Night
7 Nights - US $2,438
Cottage
4.5(2 Reviews)
1 Bedroom
1 Bath
2 Guests
- Pool
- Pet Friendly
- Air Conditioner
- Internet
US $147/Night
7 Nights - US $1,032
Cabin
2.0(1 Review)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pool
- Pet Friendly
- Kitchen
US $149/Night
7 Nights - US $1,043
Cabin
2.0(1 Review)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pool
- Pet Friendly
- Kitchen
US $148/Night
7 Nights - US $1,035
