
House vacation rentals in Caledon
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Top-rated house rentals in Caledon
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Christie St. Coach House
Located steps from Lake Ontario you will find peace and quiet at the Coach House. One of the best streets to view the sunset over Lake Ontario! A short 10min walk to Port Dalhousie business district and Lakeside Park Beach. Find all you need to eat and drink at several restaurants and cafés. Quick access to the QEW and 406 highways. Centrally located between the Wine Regions of Niagara-on-the-lake and The Bench. 15mins East or West will find you at most Niagara Wineries. Licence No: 23112230 STR

Log Cabin in the heart of downtown Elora
The Cabin Elora is a beautiful rustic log cabin stylishly updated with modern and hand made furniture from a local artisan. You will enjoy a clean, bright and open concept space. Located in the heart of Elora, walking out the door into downtown yet nestled off the street giving you wonderful privacy and a quiet peaceful atmosphere. Features: • King size bed with Egyptian cotton sheets • Private patio overlooking Metcalfe St. and gardens • Clean, stocked kitchen • Perfect downtown location

Cozy newly renovated one bedroom apt
Bring the entire family to this wonderful location with plenty of space for relaxation. The Toronto Pearson International Airport is only 22 minutes away, and major highways are nearby. A family-friendly setting, side entrance, convenient location, and walking distance to SilverCity Cinemas, Metro Supermarket, TD Bank, CIBC Bank, and a number of restaurants (including MOntanas BBQ & Bar, Hakkalious, Brar's, and others), as well as a number of clothing stores, and many more establishments.

Adorable — One Bedroom Guest Unit in Vaughan, ON
Enjoy a stylish and peaceful stay at this centrally located one-bedroom lower-level unit, perfect for both leisure and business travelers. With your private entrance, parking, and all the essentials, it’s your ideal home away from home. Features include a full kitchen, bathroom, internet, smart TV, one Queen and one sofa bed, and a functional workspace. Steps from FreshCo, Walmart, restaurants, and services. Minutes to Vaughan Mills, Canada’s Wonderland, Cortellucci Hospital and transit.

Cozy Cabin Vibes - Hot Tub• Firepit• Snowy Retreat
Escape to our riverside cabin this winter—soak in the hot tub under falling snow, curl up by the fire, and enjoy cozy evenings surrounded by nature. Perfect for couples, families, a ski weekend away, girls’ weekends, or a quiet work-from-home retreat. • Sleeps up to 8 guests comfortably • 3 cozy bedrooms (2 with private decks!) • 1.5 bathrooms • Fully equipped kitchen + BBQ patio for year-round grilling • Stylish living room with fireplace & smart TV • Fast Wi-Fi, workspace-friendly

Studio Apartment
Discover the perfect blend of comfort and convenience in this cozy studio apartment, ideally situated in the vibrant heart of Caledon. Key Features: Prime Location: Steps away from shops, cafes, and parks. Modern Amenities: Spacious living area, and stylish bathroom. Natural Light: Large windows that fill the space with warmth and brightness. Community Vibe: Enjoy the friendly neighborhood atmosphere and local events. This peaceful retreat, offers everything you need. Don't miss out!

Spacious and Comfy 2 BR Suite
Discover tranquility in our 2-bedroom legal basement apartment, nestled in Milton’s quiet and peaceful neighborhood. Enjoy an open-concept living room with 8.5 ft ceiling, and 2 roomy bedrooms; perfect for couples or families to relax in this comfortable, private, retreat. Easy access to Oakville, Burlington, Mississauga, and Toronto Pearson Airport, and minutes away from Toronto Premium Outlets, Mattamy Cycling Centre, and scenic trails, makes this location ideal for both work and play.

"Cottage Home On The River" 1 Bedroom
Welcome to Speed Island Trail! Nestled on 1 Acre property in a forested area that backs onto the Speed River. Enjoy Beautiful views all season long with large floor to ceiling windows and wildlife right outside your door. It is just like being out at the cottage. This beautiful one bedroom house is beautifully decorated, has a large kitchen and a breakfast bar. Enjoy the large sunroom and deck where you can sit back and relax. Added bonus the Chickadees eat right off your hand!

Elora Heritage House
Welcome to Elora Heritage House, where unforgettable experiences await in the heart of Elora. Built in the 19th century, our meticulously crafted home exemplifies quality and attention to detail. Discover carefully curated rooms with mid-century furniture, modern design, and a nostalgic ambiance. Nestled amidst serene trees, generous natural surroundings, world-class dining, and shops are just steps away. Embrace the essence of Elora at our cozy haven.

Elegant 2BR townhouse condo in central Oakville
Enjoy your stay in this elegant, clean, and fully equipped two bedroom and two-bathroom condo townhouse. Centrally located in Oakville and within walking distance to shops, restaurants, and parks. Beautiful upscale building in a quiet and safe neighborhood with large terrace overlooking a mature tree lined street. Abundant walking trails nearby for you to explore and enjoy. Easy access to highway 407, 403, QEW and Trafalgar GO Station.

The Rosé House NOTL - Glam room - Old Town
Welcome to the The Rosé House located in the heart of NOTL. This newly renovated 3100sqft home is the perfect to celebrate a mature Girl's Getaway! Bring your friends/family to enjoy everything NOTL has to offer! Steps to wineries, the Pedal Pub, golf courses, the lavender farm, Ice Wine Festival, restaurants, shopping, Shaw Festival Theatre and more! Niagara Falls is also within easy reach!

20%OFF| 0 Cleaning Fee| Mins to Lake| Free Parking
❥ Transportation: 🚗 5 mins to Highway 404. 🎢 20 mins to Wonderland; ✈️ 40 mins to airport. ⛳ 7 mins to Golf. ❥ Privacy: 🅿️ Driveway parking. 🌙 No sidewalks for added quiet. ❥ Amenities: 🛒 Close to Food Basics, No Frills, and 🥢 15 mins to T&T. ❥ Recreation: 🛶 Near Lake Wilcox (boating), 🏊 5 mins to Oak Ridges Center, 🌊 10 mins to Lake Wilcox & Bond Lake, 🥾 hiking trails nearby.
Popular amenities for Caledon house rentals
House rentals with a pool

Year-Round Heated Pool & Hot Tub Family Oasis

WhiteOrchid LuxuryHome WithSaltHeatedSwimmingPool

Entire Guest Unit+Free Parking by Glenbridge Plaza

The Nautical Nook | Luxury Beach House

Wine country Cottage 15 min drive to old Town NOTL

California Chic +Breathe +Unwind +Restore

Under the Whispering Pines

Chic King West Studio – TIFF & FIFA at Your Door
Weekly house rentals

Elegant & Spacious 1 Bd1Bth Private Apmt by Forest

Stunning Luxury Home

Private Basement Entrance suite

Charming Farmhouse Stunning Views & Hot tub

Spotless 100% Private House ~Trinity Plaza

LUXE by Marvalous 2

Bright & Spacious 6 BR | Private | Main Floor Bath

3BR 3.5WR | RO Water | BR with TV | Workdesk
Private house rentals

Spacious Country Retreat

Family Stay | Pool Table | Main Floor Bath & Sleep

Live Lavishly: Modern Studio, 5G, Parking

Place to Relax with whole Family

3BR Spacious Home - KING BED

Newly Renovated Cozy One Bedroom Basement APT

Cozy Campbellville

Pond View Gardens
When is the best time to visit Caledon?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ239 | ﺩ.ﺇ228 | ﺩ.ﺇ228 | ﺩ.ﺇ253 | ﺩ.ﺇ261 | ﺩ.ﺇ268 | ﺩ.ﺇ275 | ﺩ.ﺇ290 | ﺩ.ﺇ268 | ﺩ.ﺇ250 | ﺩ.ﺇ253 | ﺩ.ﺇ253 |
| 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 |
Quick stats about house rentals in Caledon

Total vacation rentals
Explore 1,060 vacation rentals in Caledon

Nightly prices starting at
Caledon vacation rentals start at ﺩ.ﺇ37 per night before taxes and fees

Verified guest reviews
Over 14,430 verified reviews to help you choose

Family-friendly vacation rentals
410 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 150 rentals that welcome pets

Vacation rentals with a pool
40 properties feature pools

Rentals with dedicated workspaces
500 properties have a dedicated workspace

Wi-Fi availability
1,020 of Caledon vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Caledon rentals

4.6 Average rating
Caledon stays receive an average rating of 4.6 out of 5 from guests

Nearby attractions
Caledon's top spots, include SilverCity Brampton Cinemas, Landmark Cinemas 7 Bolton, and Uptown Theatre
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- Rentals with pools Caledon
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- Rogers Centre
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