
House holiday rentals in Caledon
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Top-rated house rentals in Caledon
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Your Own Suite-Moderncharm Hideaways Near TorAirp
Charming Executive Suite with Large Backyard on Ravine Just minutes away from Toronto International Airport, a variety of amazing restaurants (including authentic Indian cuisine),grocery stores This suite is perfect choice for a weekend getaway, business trip, staycation, work-from-home alternative, or a cozy home base while exploring Toronto best The unbeatable location puts you 24 minutes from Downtown Toronto, 1.5 hours from Niagara Falls. And the breathtaking fall colors of North Country.

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.

Modern Executive Townhome w/ Rooftop Hot Tub Oasis
Stylish contemporary townhome in Oakville! The perfect retreat for couples, families, and friends alike. Experience the rooftop terrace, complete with a Private Jacuzzi Hot Tub that provides the ultimate relaxation experience! It's the perfect spot to unwind after a long day of sightseeing or to enjoy an evening under the stars. You'll love the stunning and spacious living areas, fully equipped kitchen, and two comfortable bedrooms. Close to Three Major Highways in a Central Location!

Spacious 3-Bed Home near Airport. Parking Backyard
Welcome to this 3-bedroom, 1-bathroom house with parking, close to the airport and amenities Enjoy a private backyard, and walk to nearby restaurants, a grocery store, and a 24/7 convenience store Minutes from Bramalea City Centre 👉The reservation holder must be 25 or older We require all guests to have verified accounts 👉For accounts with no or less than stellar reviews, a deposit might be also required. Deposits will be refunded after check-out, provided everything is in order.

"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!

Halton Hills Hideaway_Private Suite
🌿 Halton Hills Hideaway – Cozy Basement Suite Near Downtown Georgetown ✨ What You’ll Love: 🚪 Private Basement Suite – Separate entrance & no shared areas 🛏️ Queen Bed – Comfy and perfect for solo travelers or couples 🌳 Garden Views – Enjoy calming green views from your lookout window 🧼 Clean & Cozy – Thoughtfully prepared for a peaceful stay 🏘️ Charming Neighborhood – Quiet, friendly, and safe 🔍 Check the amenities section for full details—we’d love to host you!

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.
Popular amenities for house rentals in Caledon
House rentals with a pool

Luxurious 4BDRM-King Bed-Barrie-near Snow Resorts

Year-Round Heated Pool & Hot Tub Family Oasis

WhiteOrchid LuxuryHome WithSaltHeatedSwimmingPool

Entire Guest Unit+Free Parking by Glenbridge Plaza

Heart of Kimberley - with views and a hot tub

California Chic +Breathe +Unwind +Restore

Cozy Modern Suite•Heated Flrs•Game Rm•Free Pkg

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

Stonewell Farm Guest House

2 Bedroom Basement Apartment with Modern Amenities

Modern Stay Brampton Luxurious (Basement)

A Private Oasis with Fireplace

Place to Relax with whole Family

LUXE by Marvalous 2

Luxurious 5 Bedroom Estate on 2 Acres

Entire Lower Level Home 3500 Sq Walk Out
Private house rentals

Elegant & Spacious 1 Bd1Bth Private Apmt by Forest

Beautiful & Cozy 3-Bedroom Getaway in Brampton

Perfect@2, Comfortable @4

Family Stay | Pool Table | Main Floor Bath & Sleep

serene ravine breeze

Live Lavishly: Modern Studio, 5G, Parking

3BR Spacious Home - KING BED

3BR 3.5WR | RO Water | BR with TV | Workdesk
When is the best time to visit Caledon?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $83 SGD | $80 SGD | $80 SGD | $89 SGD | $91 SGD | $94 SGD | $96 SGD | $101 SGD | $94 SGD | $87 SGD | $89 SGD | $89 SGD |
| 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 holiday rentals
Explore 1,060 holiday rentals in Caledon

Nightly prices starting at
Caledon holiday rentals start at $13 SGD per night before taxes and fees

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

Family-friendly holiday rentals
410 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 150 rentals that welcome pets

Holiday rentals with a pool
40 properties feature pools

Rentals with dedicated workspaces
500 properties have a dedicated workspace

Wifi availability
1,020 of Caledon holiday rentals include wifi 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
Destinations to explore
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- Rentals with a hot tub Caledon
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- Rentals with pools Caledon
- Rentals with a washing machine and dryer Caledon
- Rentals with lake access Caledon
- Apartment rentals Caledon
- Bed and breakfasts Caledon
- Guest house rentals Caledon
- Rentals with a fireplace Caledon
- Rentals with a patio Caledon
- Flat rentals Caledon
- Rentals with an EV charger Caledon
- Rentals with outdoor seating Caledon
- Waterfront rentals Caledon
- Smoking-friendly rentals Caledon
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- House rentals Peel
- House rentals Ontario
- House rentals Canada
- Rogers Centre
- CN Tower
- Scotiabank Arena
- University of Toronto
- Blue Mountain Village
- Metro Toronto Convention Centre
- Distillery District
- Port Credit
- The Danforth Music Hall
- Exhibition Place
- Harbourfront Centre
- BMO Field
- Toronto Zoo
- Toronto Eaton Centre
- Trinity Bellwoods Park
- Massey Hall
- Financial District
- Casa Loma
- Whistle Bear Golf Club
- Dufferin Grove Park
- Snow Valley Ski Resort
- Toronto City Hall
- Rouge National Urban Park
- Beaver Valley Ski Club




