Home Vacation Rentals By Owner In Caledon, ON

Showing 20 Of 30 Vacation Rentals
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Exceptional(1)

$130.88

/ Nightly
Apartment

Your Luxurious Caledon escape close to everywhere

Caledon, Ontario, Canada

Discover the best of Caledon from our perfectly situated home in the heart of Southfields Village. Our location seamlessly blends convenience with the unique charm of the area, promising a fulfilling and stress-free stay.brbrIt is few minutes away from Toronto Pearson Airport and close to all major Cities in Ontario.brbrStep outside and immediately connect with the local scene. Start your mornings with the tempting aromas from Golden Star Bakery, a nearby treasure offering delicious pastries and a taste of Caledon's authentic flavor. For your coffee or a quick meal, the familiar comfort of Tim Hortons is also within easy reach. When it's time for a more substantial meal, explore the diverse culinary options at Mint Leaf, a local favorite.brbrFor added ease, the Fresh Food Centre is conveniently located, making grocery shopping and stocking up on necessities a simple task. This prime location allows you to spend less time on errands and more time enjoying your Caledon experience.brbrFamilies will appreciate the proximity to Lina Marino Park, a wonderful green space perfect for children's play and family time outdoors. The presence of reputable schools like SouthFields Village Public School and St. Rita further underscores our home's appeal for families seeking a comfortable and well-connected base.brbrBeyond the everyday amenities, Caledon's distinct character awaits exploration. Discover unique local fashion boutiques offering a glimpse into the area's style. Treat yourself to relaxation and rejuvenation at Venus Salon & Spa. History buffs will find the Great War Flying Museum, a short trip away, a captivating destination offering insights into aviation history.brbrWhether you're seeking a peaceful retreat, an exciting family getaway, or an opportunity to immerse yourself in the authentic charm of Caledon, our home provides the ideal starting point. Enjoy the comfort and welcoming ambiance of our property, with the best of the neighbourhood's attractions and conveniences right at your doorstep. brbrSecure your Caledon escape today and unlock the local treasures that await!
Bed 2

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Bath 1

Bath

Sleep 4

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$179.19

/ Nightly
Lodge

Unique Vacation Rental Suite with a Patio in Terra Cotta, Ontario

Caledon, Caledon, Canada

This wonderful suite, within a vacation rental, has a patio and is set in the village of Terra Cotta, Ontario, just an hour from Toronto, and less than two hours from the famous Niagara Falls waterfalls. Guests are just a few minutes walk from the Terra Cotta Provincial Park, and the Caledon Rail Trail. The rental also overlooks the Credit River where guests can fish and take part in other watersports as well. brbr brbrThe master bedroom has a queen-size bed, while the second room has two twin beds, making the rental ideal for families. The two bedrooms both have ample storage so guests can fully unpack and place their luggage on the provided racks and forget about it until the end of their vacation. There is one full bathroom, shared between the two rooms, which can also be booked separately depending on availability. brbr brbrGuests can relax in the living area and enjoy a board game or a game of cards, as well as choosing a book from the hosts' selection to unwind at the end of a long day of excursions and activities. There are stunning views around the rental of all the woodland and the river surrounding the rental. Both of the rooms lead out onto a patio so guests can sit out and enjoy these tranquil surroundings. brbr brbrThe hosts have provided everything a 21st-century traveler could need during their stay. There is a drinks refrigerator which is kept fully-stocked with a selection of water, juices, and soft drinks. Guests are allowed to bring their own alcoholic beverages to keep in the refrigerator as well. The property has air conditioning and heating so guests will be comfortable all through the year. There is Wi-Fi for guests to use, and even a printer should they need to print tickets or boarding passes. There is a shared living space that guests can relax in, and they are free to borrow any of the books they might find there as well.
Bed 1

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Bath 1

Bath

Sleep 4

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Exceptional(11)

$275.15

/ Nightly
Apartment

Cozy 3BR Caledon Bsmt Suite w/ Private Access & Basketball Court—Near Brampton!

Caledon, Ontario, Canada

Book this listing directly at www.kozinestrentals.com and save up to 20%brbrWelcome to our fully furnished 3-bedroom, 2-bath basement suite in the peaceful neighbourhood of Caledon—just minutes from Brampton, Hwy 410, and local shops & eateries. Enjoy fast WiFi & Smart TVs with streaming options. For guests who love staying active or enjoy nature, step outside to the Etobicoke Creek Trail right behind the home for scenic views, or shoot hoops on the basketball net in our spacious backyard. Perfect for families & friends seeking comfort, convenience, and outdoor fun!brbrThe apartment boasts a spacious living room with comfortable seating, a large flat-screen TV, and plenty of natural light that floods through the windows. The kitchen is fully equipped with all the necessary appliances, including a refrigerator, stove, oven, microwave, and dishwasher. It also has ample counter space and cabinets for storing groceries and cooking supplies.brbrEach of the three bedrooms comes with a comfortable bed, fresh linens, and plenty of closet space for storing your belongings. The master bedroom has a private en-suite bathroom, while the other two bedrooms share a separate full bathroom. Both bathrooms are equipped with all the necessary amenities, including towels, toiletries, and a hairdryer.brbrOther amenities that guests can enjoy include free Wi-Fi, air conditioning, heating, and a washer and dryer for laundry needs. The apartment also has a private entrance, ensuring that guests can come and go as they please without any disturbance.
Bed 3

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Bath 2

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Sleep 7

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$430.66

/ Nightly
Private Vacation Home

Detached 5 Bedroom ~100% Spotless ~Sleeps 13

Caledon, Ontario, Canada

Enjoy Comfort in our Private 5BR & 4.5WR Caledon Home - Perfect for family & friends gatherings surrounded by nature!brbr✓ Entire home to yourself – 100% privacybr✓ 5 spacious bedrooms – sleeps up to 13 guests!br✓ 4.5 modern washroomsbr✓ Fully equipped kitchen with all cooking essentialsbr✓ Large Smart TV & High-Speed Wi-Fi for streamingbr✓ Books & Cards for cozy family timebrbrBook your stay today & create unforgettable memories in comfort and style!brbrWe have a smart lock for your quick access to the house. We will send you complete check-in instructions, guest guide link, etc, 1.5 days before your check-in. we can also be present if needed as we live in same town. brbrResidential, upscale: This is a new home subdivision (“Castles of Caledon”) with large detached houses, many with high‑end finishes. brbrSuburban with green space: Parks, natural reserves and conservation areas are nearby. The area seems planned with amenities, open spaces, and a generally tranquil suburban character.brbrGuests will have complete access to the entire house. Feel free to make the most of the available amenities, allowing for a comfortable and enjoyable stay.brbrNote: Basement is unfinished and not accessible to guests.brbr✨ Spacious 5-Bedroom & 4.5-Washroom Home | Full Privacy | Sleeps 13 | Books | Playing cards ✨brbrWelcome to your perfect family getaway! This beautifully decorated 5-bedroom Caledon home combines comfort, style, and space to give you the ultimate relaxing and fun-filled stay.brbr✔ 5 Bedrooms, 4 Full + 1 Half Washrooms – plenty of room for everyone to unwindbr✔ Fully Private Home – enjoy total privacy with no shared amenitiesbr✔ Books & Playing cards – perfect for entertainment and cozy nights inbr✔ Professionally Cleaned – fresh linens and towels for every staybr✔ Free Parking – up to 4 vehicles on the driveway and 2 in the garagebrbr MAIN FLOORbr✔ Family Room with a 75-inch Smart TV and comfy sofabr✔ Cozy Living Room for quality time togetherbr✔ Fully Equipped Kitchen with all cooking essentials + 2 island chairsbr✔ Dining Area 1: Seats 6br✔ Dining Area 2: Seats 6br✔ Bedroom 1: Queen bedbr✔ 1 Half Washroombr✔ Access to a Garage brbr UPPER LEVEL (2ND FLOOR)br✔ Bedroom 2: Master suite with King bed + 1 twin bed + 2 cozy chairs + private ensuite full washroom with bathtubbr✔ Bedroom 3: Queen bed + 1 cozy chair + attached full washroom with bathtubbr✔ Bedroom 4: Queen bed + attached full washroom with bathtubbr✔ Bedroom 5: Double bed + 1 bunk bed (sleeps 2) + attached full washroom with bathtubbr✔ Laundry Room with washer and dryerbrbr LOWER LEVELbrBasement is not finished and is not accessible to guests.brbr CLEANING & SAFETYbrOur home is professionally cleaned and disinfected before every guest arrives. All linens (sheets, pillowcases, duvet covers, towels) are freshly washed. We also provide extra cleaning supplies for your peace of mind.brbrNOTE: We offer housekeeping/cleaning service daily at an additional cost to our guests: $260 for regular cleaning and $200 for basic (no laundry). brbr PARKINGbrFree parking for up to 4 vehicles on the driveway and 2 vehicles in the garage. brbr TOTAL PRIVACYbrYou’ll have exclusive access to the entire home—main floor and upper level. No shared entrances. No other tenants. Just you and your guests.brbrWhether you're travelling with family, friends, or colleagues, this spacious and well-appointed home offers everything you need for a relaxing and memorable stay.brbr✅ Book now with confidence. We’re excited to host you!brbrTo help us keep the home in perfect condition for all guests, we kindly ask that you:brbr- Leave everything as you found it upon arrival.br- Do not move any furniture in the house.br- No pets are allowed br- No parties, events, or gatherings br- Quiet times are 11pm to 7am, please be respectful of the neighbors br- No smoking, vaping, or e-cigarettes are allowed inside the propertybr- If smoking outside, please clean upbrWe truly appreciate your cooperation and understanding - it helps us maintain an excellent experience for everyone!
Bed 5

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Bath 4

Bath

Sleep 13

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Exceptional(1)

$355.16

/ Nightly
Private Vacation Home

Luxury 5-Bed Home w/ Office & 5 Baths | Peaceful Caledon Escape

Caledon, Ontario, Canada

Welcome to your home away from home in beautiful Caledon — a peaceful, upscale community surrounded by rolling countryside and minutes from city conveniences. This spacious 5-bedroom, 5-bath executive home with a private office offers the perfect blend of comfort, style, and functionality for families, groups, or professionals seeking a relaxing extended stay.brbrStep inside to an open-concept main floor filled with natural light, featuring a modern kitchen with stainless steel appliances, quartz countertops, and a large island perfect for family meals or entertaining. The adjoining living and dining areas provide plenty of room to gather, while the office offers a quiet, private space for remote work or study.brbrEach of the five bedrooms is thoughtfully designed for comfort, with plush bedding, ample storage, and tasteful décor. The primary suite includes a luxurious ensuite bath and walk-in closet, while additional bathrooms ensure privacy and convenience for every guest.brbrEnjoy the spacious backyard and peaceful surroundings, ideal for unwinding after a long day. The home is located close to local parks, hiking trails, restaurants, and shopping, with easy access to major routes connecting to Brampton, Mississauga, and Toronto.brbrWhether you’re booking for a family getaway, corporate relocation, or temporary stay after home repairs or insurance work, this Caledon retreat provides all the comforts and amenities you need — including Wi-Fi, laundry, driveway parking, and fully furnished spaces ready for move-in.brbrExperience modern living in one of Caledon’s most desirable neighbourhoods — a perfect balance of tranquility, convenience, and home-like warmth.
Bed 5

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Bath 5

Bath

Sleep 11

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$294.76

/ Nightly
Private Vacation Home

Relaxing 5BR & 4.5WR Detached Home | Sleeps 13

Caledon, Ontario, Canada

Enjoy Comfort in our Private 5BR & 4.5WR Caledon Home - Perfect for Families & Groups!brbr✓ Entire home to yourself – 100% privacybr✓ 5 spacious bedrooms – sleeps up to 13 guests!br✓ 4.5 modern washroomsbr✓ Fully equipped kitchen with all cooking essentialsbr✓ Large Smart TV & High-Speed Wi-Fi for streamingbr✓ Books & Cards for cozy family timebrbrBook your stay today & create unforgettable memories in comfort and style!brbr✨ Spacious 5-Bedroom & 4.5-Washroom Home | Full Privacy | Sleeps 13 | Books | Playing cards ✨brbrWelcome to your perfect family getaway! This beautifully decorated 5-bedroom Caledon home combines comfort, style, and space to give you the ultimate relaxing and fun-filled stay.brbr✔ 5 Bedrooms, 4 Full + 1 Half Washrooms – plenty of room for everyone to unwindbr✔ Fully Private Home – enjoy total privacy with no shared amenitiesbr✔ Books & Playing cards – perfect for entertainment and cozy nights inbr✔ Professionally Cleaned – fresh linens and towels for every staybr✔ Free Parking – up to 4 vehicles on the driveway and 2 in the garagebrbr MAIN FLOORbr✔ Family Room with a 75-inch Smart TV and comfy sofabr✔ Cozy Living Room for quality time togetherbr✔ Fully Equipped Kitchen with all cooking essentials + 2 island chairsbr✔ Dining Area 1: Seats 6br✔ Dining Area 2: Seats 6br✔ Bedroom 1: Queen bedbr✔ 1 Half Washroombr✔ Access to a Garage brbr UPPER LEVEL (2ND FLOOR)br✔ Bedroom 2: Master suite with King bed + 1 twin bed + 2 cozy chairs + private ensuite full washroom with bathtubbr✔ Bedroom 3: Queen bed + 1 cozy chair + attached full washroom with bathtubbr✔ Bedroom 4: Queen bed + attached full washroom with bathtubbr✔ Bedroom 5: Double bed + 1 bunk bed (sleeps 2) + attached full washroom with bathtubbr✔ Laundry Room with washer and dryerbrbr LOWER LEVELbrBasement is not finished and is not accessible to guests.brbr CLEANING & SAFETYbrOur home is professionally cleaned and disinfected before every guest arrives. All linens (sheets, pillowcases, duvet covers, towels) are freshly washed. We also provide extra cleaning supplies for your peace of mind.brbrNOTE: We offer housekeeping/cleaning service daily at an additional cost to our guests: $260 for regular cleaning and $200 for basic (no laundry). brbr PARKINGbrFree parking for up to 4 vehicles on the driveway and 2 vehicles in the garage. brbr TOTAL PRIVACYbrYou’ll have exclusive access to the entire home—main floor and upper level. No shared entrances. No other tenants. Just you and your guests.brbrWhether you're travelling with family, friends, or colleagues, this spacious and well-appointed home offers everything you need for a relaxing and memorable stay.brbr✅ Book now with confidence. We’re excited to host you!
Bed 5

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Bath 4

Bath

Sleep 13

Sleeps

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$714.11

/ Nightly
Private Vacation Home

Luxury 4BR Stay with Swim Spa, Golf & Fireplaces

Caledon, Ontario, Canada

Summary:brbrKick back in style at this spacious home packed with fun + comfort! Swing in the golf simulator, unwind in the swim spa, or catch a movie on one of the projectors. Grill & chill on multiple patios with a fountain view, or cozy up by the double-sided fireplace with 4 bedrooms (5 beds + crib), 3 baths, a full gym space, and tons of parking. Just minutes from nature trails, golf courses, and charming local spots! brbrbrbrGuests will need to bring their own golf clubs as none are provided.brbrbrbrThe Space:brbr✪ Property Overviewbrbr➜ Approx. 5000 ft² / 465 m² of space. Designed for comfort and entertainment.brbr➜ Packed with lifestyle features including a private golf simulator, gym space, double-sided fireplace, 2 projectors, and multiple TVs.brbr➜ Dedicated workspace, perfect for remote work or focused tasks.brbr➜ Outdoor living at its best with a swim spa, fountain, BBQ grill, several patios, and cozy seating areas perfect for relaxing or entertaining.brbr➜ Complimentary parking for 6+ vehicles in the driveway and carport.brbrbrbr✪ Sleeping Arrangementsbrbr➜ The master bedroom features a king bed, double-sided fireplace, and an en-suite bathroom.brbr➜ Bedroom 2 features a queen bed on the main floor.brbr➜ Bedroom 3 features a king bed on the top floor.brbr➜ Bedroom 4 features a double bunk bed on the top floor.brbr➜ A crib is available for little ones.brbrbrbr✪ Living and Working Spacebrbr➜ Equipped with TVs and 2 projectors for movies, sports, and streaming.brbr➜ High-speed internet access and smart NEST thermostats.brbr➜ Dedicated workspace, quiet environment.brbr➜ Spacious living room with comfortable seating, plus gym and golf simulator for work-play balance.brbrbrbr✪ Bathroomsbrbr➜ 3 clean and sanitized bathrooms, including one with a bathtub.brbrbrbr✪ Kitchen and Diningbrbr➜ Fully equipped kitchen with 2 fridges, stove, oven, microwave, and essentials.brbr➜ Spacious dining table with seating for the whole group.brbrbrbr✪ Amenitiesbrbr➜ In-house washer and dryer machines.brbr➜ Full sets of hotel-quality sheets, duvets, and plenty of towels.brbr➜ Swim spa, multiple patio areas, and a fountain feature.brbrbrbr✪ Location and Accessibilitybrbr➜ Close proximity to scenic trails, golf courses, and nature escapes.brbr➜ Short drive to shopping, dining, and family-friendly attractions.brbrbrbr➤ IMPORTANT NOTE FOR 1 WEEK STAY OR LONGER:brbrToilet paper, garbage bags, and basic toiletries will be provided for the guests at the beginning of the stay. It will then be the guest's responsibility to provide for these for the remainder of their stay.brbrbrbrGuest Access:brbr➤ Guests will have access to the entire unit. Please, make yourself at home.brbrbrbr➤ Availability of free 6+ spots in driveway and carport.brbrbrbrThe Neighborhood:brbrNestled in the heart of Caledon, this area blends small-town charm with stunning natural beauty. Rolling hills, scenic trails, and conservation areas make it perfect for outdoor lovers looking to hike, bike, or simply unwind in a peaceful setting.brbrbrbrThe community offers a relaxed atmosphere with local markets, cozy cafés, and family-owned restaurants nearby. Whether you’re looking for farm-to-table dining or a quick coffee stop, you’ll find plenty of inviting options.brbrbrbrFor those seeking more activity, golf courses, equestrian centers, and cultural spots are all within easy reach. You’ll enjoy a mix of nature, leisure, and local character that makes every stay memorable.brbrbrbrGetting Around:brbr➜ Car is the most convenient way to explore Caledon and beyond.brbrbrbr➜ Ample parking available on-site for multiple vehicles.brbrbrbr➜ Local taxi and rideshare services operate in the area.brbrbrbr➜ Regional bus routes connect to nearby towns and hubs.brbrbrbr➜ Cycling is a great option with scenic country roads and trails.brbrbrbrOther Things to Note:brbr➤ The property is equipped with both heating and air conditioning; however, we cannot guarantee that you will achieve a comfortable temperature if your preference falls outside the range of approximately 17 to 25 degrees Celsius. Additionally, due to the nature of short-term rentals, where guests may frequently come and go, we cannot promise 100% uptime, as some guests may inadvertently push the systems beyond their capacity, necessitating repairs.brbrbrbr➤ Unfortunately, I can't offer a bag drop-off service. For those arriving early or having a late flight, you can use bagbnb site to find options to drop off your bag for a fee.brbrbrbr➤ Please keep in mind that I am not responsible for any packages you order to the unit.brbrbrbrInteraction with Guests:brbrI will be your personal concierge for your stay. If you have any questions, you’re lost, or just need some great recommendations, I’ll be there for you around the clock.
Bed 4

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Bath 3

Bath

Sleep 8

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Exceptional(3)

$372.72

/ Nightly
Private Vacation Home

Fall Nordic Cottage Retreat with Hot Tub 60 Minutes from City

Caledon, Ontario, Canada

Nestled in Caledon, this lovely house offers 2 cozy bedrooms with a king and queen bed. With 3 bathrooms equipped with luxurious amenities like a bidet and hair dryer, guests can relax in style. Whether you're looking to unwind in the spacious living area or enjoy the fresh air in the backyard, this awesome property has everything you need for a memorable getaway. Make your holiday one for the books with a stay at our place.brbrYou'll have the entire home to yourself to enjoy. There is a separate apartment on the property that is rented long-term, but the tenant is rarely home and does not use any of the guest areas. He simply comes and goes and does not spend time outside, so your privacy will not be affected.brbrEnjoy crisp fall evenings on the patio, cozy blankets included brbrUnwind on a peaceful 8-acre property just 1 hour from Toronto.br• 8 mins from TOC Osprey br• Cozy living area with electric fireplacebr• 2 primary bedrooms with ensuitesbr• Starlink Wi-Fi br• Smart TVbrbrStart your morning on the patio, stroll private & nearby trails, A perfect escape for families, nature lovers, golfers, and anyone seeking a calm, stylish retreat outside the city.brbrBedroom 1: King bed with EnsuitebrbrBedroom 2: Queen bed with EnsuitebrbrPlease note: The house runs on a septic system, so while the plumbing works perfectly, we kindly ask that you avoid overloading the toilets with excessive toilet paper or non-flushable item
Bed 2

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Bath 2

Bath

Sleep 4

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