1. Canada
  2. Ontario
  3. Owen Sound
  4. Chesley
  5. Rentals by Owner

Chesley Rentals by Owner

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10.0 (4 Reviews)
House
  • Parking
  • Security/Safety
  • Sports/Activities
8.0 (1 Review)
House
  • Pet Friendly
  • Security/Safety
  • Bedding/Linens

Why Choose Rent By Owner for your Chesley vacation rental?

What makes our Rentals by Owner special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

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

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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.

Average Temperature Daytime: 22°C - Nighttime: 13°C
autumn
Fall (September to November)

Experience the vibrant fall foliage during this peak season, attracting nature lovers and those seeking scenic views in this region.

Average Temperature Daytime: 16°C - Nighttime: 7°C

Off-Season Highlights

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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.

Average Temperature Daytime: -3°C - Nighttime: -10°C
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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.

Average Temperature Daytime: 9°C - Nighttime: 2°C

Weekly Weather Forecast for Chesley

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.

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.
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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.
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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

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?

The cancellation policy varies depending on the individual owner’s terms listed on the property page. It is recommended to review the specific cancellation details when booking and contact the owner directly if you have any questions about refunds or cancellation deadlines.

4. How do I communicate with the owner before booking my stay in Chesley?

You can reach out to the owner through the messaging feature on the Rent By Owner platform. This allows you to ask questions about the rental property, availability, and any special requirements before finalizing your reservation.

5. Are there any additional fees or charges when booking a vacation rental here?

Additional fees such as cleaning fees, security deposits, or service charges are typically detailed on the listing. It’s best to review all costs prior to booking to understand the total price and contact the owner if you need clarification.

6. What amenities are usually included in rentals by owner in this area?

Amenities vary by property but commonly include essentials like Wi-Fi, parking, kitchen facilities, and linens. Check each listing carefully for specific amenities offered and confirm any special requirements you may have.

7. Is there a minimum stay requirement for properties in Chesley, Ontario?

Minimum stay requirements depend on the individual owner and the specific rental listing. These details are specified on the property page, so be sure to review them before booking or contact the owner if you need further information.