- Canada
- Ontario
- Owen Sound
- Chesley
- Rentals by Owner
Discover Your Ideal Rental by Owner in Chesley, Ontario for a Comfortable Stay
Discover Your Perfect Chesley Rentals by Owner
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Rentals by Owner
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Luxury Vacation Rentals
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Pet Friendly Vacation Rentals
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Chesley Rentals by Owner
- Security/Safety
- Bedding/Linens
- Wellness Facilities
- Parking
- Security/Safety
- Sports/Activities
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- View
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Bedding/Linens
- Fireplace/Heating
- Parking
- Pet Friendly
- Security/Safety
- Air Conditioner
- Parking
- TV
- Parking
- Security/Safety
- Bedding/Linens
- Pet Friendly
- Security/Safety
- Bedding/Linens
- Air Conditioner
- Parking
- TV
Why Choose Rent By Owner for your Chesley vacation rental?
What makes our Rentals by Owner special?
Best Times to Visit Chesley
When should you plan your Rentals by Owner stay?
Timing your visit to this region can significantly enhance your experience, so consider the seasonal climate and local events when booking your Rent By Owner rental in Chesley, Ontario, to ensure a memorable and enjoyable vacation.
Peak Season Highlights
Summer (June to August)
This is the busiest time when visitors flock to Chesley to enjoy warm weather and outdoor activities, making it an ideal period for a lively experience in the area.
Fall (September to November)
Experience the vibrant fall foliage during this peak season, attracting nature lovers and those seeking scenic views in this region.
Off-Season Highlights
Winter (December to February)
During the winter months, the area offers a quieter atmosphere, perfect for travelers looking for a peaceful retreat away from peak crowds.
Spring (March to May)
As the region transitions into spring, fewer visitors venture here, creating an excellent opportunity for a serene stay amid blooming landscapes.
Weekly Weather Forecast for Chesley
How to Book Your Chesley vacation rental
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Chesley
Common Rentals by Owner Amenities
What amenities can you expect?
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
- You can enjoy spacious outdoor seating areas perfect for relaxing or dining al fresco in the region.
- Many rentals feature private patios or decks where you can unwind while taking in the natural surroundings.
- Expect to find a barbecue grill available, ideal for preparing meals outdoors during your stay.
- Some properties offer easy access to nearby gardens or landscaped yards to explore and enjoy.
- You might have the opportunity to use outdoor fire pits for cozy evenings under the stars.
- In this area, rentals often include parking spaces with convenient access to outdoor amenities.
- Look for properties that provide outdoor recreational equipment such as bikes or fishing gear to explore the scenic region.
Top Attractions Around Chesley
What attractions are nearby?
Enjoy a variety of outdoor activities and local attractions nearby, making it easy to explore and experience the best of this destination during your stay.

Family Activities
- Chesley Community Pool: Enjoy a fun-filled day swimming and relaxing at the local community pool, perfect for families seeking outdoor leisure activities in this welcoming area.
- MacNeill Park: Explore this scenic park featuring playgrounds, open green spaces, and walking trails that make it an ideal spot for family picnics and outdoor play here in the region.
- Local Heritage Museum: Discover the area's history through engaging exhibits and interactive displays that entertain and educate children visiting this destination.
- Nearby Trails and Nature Reserves: Venture into the natural beauty of the surroundings by exploring nearby trails and reserves that offer family-friendly hikes and wildlife viewing opportunities.
Adult Activities
- Local Winery Tours: Enjoy tasting sessions and explore the vibrant wine scene right in this region, ideal for a relaxing adult day out.
- Golfing Experiences: Tee off at nearby golf courses offering scenic views and challenging fairways, perfect for outdoor enthusiasts seeking leisure.
- Art Galleries and Studios: Discover contemporary and traditional artworks within galleries that showcase local talent and cultural heritage here.
- Historical Landmarks: Explore significant sites that reveal the area's rich history and offer engaging stories for history buffs visiting the region.
Chesley Travel Tips
How Can You Make the Most of Your Stay?
- Explore local outdoor activities: Take advantage of the area's natural beauty by engaging in nearby hiking, biking, or exploring scenic trails to fully enjoy your stay.
- Connect with community events: Check out local gatherings or seasonal festivities to immerse yourself in the region’s vibrant culture and meet fellow visitors and residents.
- Plan ahead for essentials: Stock up on necessary supplies and familiarize yourself with nearby shops to ensure a comfortable and hassle-free experience during your visit.
- Choose accommodations wisely: Opt for a rental by owner that offers personalized amenities to enhance your comfort and provide an authentic stay here in the region.
Transportation Options
- Chesley Bus Service: This local bus service offers convenient transportation within the area and connects you to nearby towns for easy exploration.
- Ontario Northland Transit: Providing regional bus routes, this option is ideal for traveling between Chesley and larger cities across Ontario with comfort and reliability.
- Private Car Rentals: Renting a car locally grants you flexible access to the region's scenic sights while staying comfortably connected during your stay.
- Taxis and Rideshare Services: Taxis and ridesharing apps are readily available here, offering quick and dependable transportation options throughout the destination.
Local Customs Options
- Traditional Maple Tapping: You can experience the local custom of tapping maple trees, a practice that reflects the area's rich history in maple syrup production.
- Community Gatherings: Participating in seasonal festivals and community events allows you to engage with the warm hospitality characteristic of this region.
- Local Craftsmanship: Supporting artisans by exploring handcrafted goods highlights a tradition of craftsmanship prevalent throughout the area.
- Respect for Nature: Properly observing outdoor etiquette and conservation efforts is part of respecting the natural landscape that defines this destination.
Frequently Asked Questions About Chesley Rentals by Owner
1. What are the top vacation rentals in Chesley?
There are a lot of options in Chesley. If you plan on staying in the Chesley area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Chesley:
- Find peace, comfort, and privacy at our spacious countryside home nestled in the heart of nature in Chatsworth!
- Little Cabin in the Pines
- Secluded 3 bedroom bungalow on the Saugeen River with 85-acres.
- GLOBALSTAY New houses near Huron Lake
- Country retreat with 50 acres on the Saugeen River.
- Waterfront Bliss Firepit and BBQ
- Comic House with Climbing Wall & Themes
- Cozy 2 bedroom river view suite with licensed restaurant on site
- Williamsford Blacksmith Shop
- Rustic Rural Retreat
2. How many Rentbyowner vacation rentals are available in Chesley?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 17 in the Chesley 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 Chesley.
3. What is the cancellation policy for a rental by owner in Chesley, Ontario?
4. How do I communicate with the owner before booking my stay in Chesley?
5. Are there any additional fees or charges when booking a vacation rental here?
6. What amenities are usually included in rentals by owner in this area?
7. Is there a minimum stay requirement for properties in Chesley, Ontario?
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- Air Conditioner
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- TV
- Bedding/Linens
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