House holiday rentals in Caledon

Indoor Pool • Hot Tub • Heated Dome • 40 min GTA

Welcome to a peaceful 15-acre retreat in Erin, featuring 3+1 bedrooms and 5 bathrooms, plus a year-round heated indoor pool 🏊‍♀️. Enjoy scenic woodland trails, a heated indoor sports dome for mini soccer & volleyball ⚽🏐, and an outdoor wood-burning hot tub with beautiful views over a spring-fed pond 🐟. Complimentary breakfast items included, and support is always available by call or message. Perfect for families and friends—ideal for relaxing getaways, small reunions, and nature escapes.

Little blue haven

Nestled in the peacful village of Alton, this home is the perfect base to explore all the area has to offer. Planning a wedding? you'll find several beautiful nearby wedding venues just minutes away. For relaxation and pampering, local spas provide indulgent treatments, while golf enthusiasts can enjoy nearby championship courses. Outdoor lovers will delight in hiking trails, mountian biking and winter skiing. Foodies can explore breweries, wineries, restaurants. Art lovers can visit galleries

Cozy Fall Escape | HotTub + Fire Pit + River

Escape to the countryside this fall! Unwind in the hot tub under the stars, gather around the fire, and wake up beside the Credit River. Just under an hour from Toronto! Perfect for a relaxing getaway, girls weekend, or 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

Indoor Pool & Hot Tub Villa | Sleeps 14

Caledon Villa — your private luxury escape, perfect for group stays with premium comfort. This spacious retreat features a heated pool, hot tub, theater, pool table, giving family and friends room to gather, play, and unwind. Everything you need is right here: ✓ Heated pool & hot tub ✓ Home theater & large TV ✓ Pool table & foosball ✓ Exercise equipment ✓ BBQ, fire pit & cozy patio ✓ Board games & basketball hoop ✓ Fully equipped kitchen Book your stay today and create lasting memories.

The Urban Nest

The Urban Nest: Spacious 3BR Oasis Close to YYZ⁠ 📍 PERFECTLY POSITIONED FOR TRAVEL & ENTERTAINMENT: Located in a vibrant, accessible area of Brampton, you are minutes away from excellent local dining, shopping, and major transit routes. If you are in town for big games or events, you will love how easily you can navigate to the main venues while returning to a quiet, peaceful neighborhood at night. Our summer calendar fills exceptionally fast. Secure your stay at The Urban Nest today!

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!

"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!

8 Acre Retreat | 5 min to TPC Osprey + Hot Tub!

Enjoy peaceful summer evenings on the patio ☀️ surrounded by nature on a private 8-acre property only 1 hr from Toronto. • 8 min from TPC Osprey 🏌️ • 2 spacious primary bedrooms w ensuites • Electric fireplace • Starlink Wi-Fi 🌟 • Smart TV • Private & nearby nature trails Start your mornings w coffee on the patio. Spend the day exploring trails or golfing nearby, then unwind at your calm, stylish retreat. Perfect for families, couples, & golfers looking to escape the city.

100% privacy 7 bed 6 bath with 7 beds Brand new

Bring the whole family to this great place with lots of room for fun. Welcome 7 Bed, 6 Bath Modern Luxurious Detached House ✓ almost Brand New Modern design with an open-concept layout ✓ Fully equipped kitchen ✓ Cozy and peaceful family room with a large flat-screen TV, Netflix , games table ✓ extra high speed internet ✓ Convenient location, safe neighborhood, easy access to major highways ✓ Comfortable 7 beds with high-quality linens ✓ Free parking for 4 plus cars

Modern Family Home•Fireplace•Backyard•NearBrampton

Enjoy a comfortable 3-bedroom family home designed for relaxing stays, featuring a private backyard, cozy fireplace, fully equipped kitchen, fast Wi-Fi, and convenient parking. Perfect for families, wedding guests, hockey tournaments, business travellers, visiting relatives, relocations, and extended stays. Prime location just 2 minutes from local shops, 20 minutes to Mississauga, and approximately 30 minutes to Toronto—making it an ideal home base for your stay.

Modern- Cozy House by Nature for Full Family of 13

Enjoy Comfort in our Private 5BR & 4.5WR Caledon Home - Perfect for family & friends gatherings surrounded by nature! ✓ Entire home to yourself – 100% privacy ✓ 5 spacious bedrooms – sleeps up to 13 guests! ✓ 4.5 modern washrooms ✓ Fully equipped kitchen with all cooking essentials ✓ Large Smart TV & High-Speed Wi-Fi for streaming ✓ Books & Cards for cozy family time Book your stay today & create unforgettable memories in comfort and style!

Mono Forest Stay & Spacious House

⭐Welcome to our 4BR, 2.5 bath Detached house near Island Lake & Hockley Valley in Orangeville, featuring: ✔ Fully equipped huge kitchen for preparing meals ✔ Cozy family room with a Smart TV ✔ High-speed internet ✔ Comfortable bedrooms with fresh linens ✔ Ping-pong, board games, treadmill, BBQ, deck, and forest views ✔ Ideal for families, groups, or wedding guests. Book your stay with confidence and make unforgettable memories!