House vacation rentals in Caledon

Modern 3BR Retreat - Walk to Trails & Rec Centre

Relaxing 3BR Home near Trails and Rec Unwind in this stylish 3 Bedroom, 2.5 bath retreat in the heart of Caledon. Perfect for families or small groups, the home features a cozy fireplace, a private backyard ideal for entertaining, and spacious living areas for your comfort. Enjoy nearby scenic trails, a modern community centre, library, gym, shops, and local cafe - all just mins of walk away. With 2-car parking included, you will have everything you need for a convenient and comfortable stay.

Hockley Valley - Jazzy Pines - 4 BR with Pool

Welcome to your private retreat in the heart of Hockley Valley! Nestled on 9 acres of rolling countryside, this unique two-story home offers breathtaking views, direct access to nature trails, and a perfect blend of rustic charm and modern comfort. The great room boasts floor-to-ceiling cathedral windows, flooding the space with natural light and offering panoramic views of the surrounding landscape. Step outside to your own oasis: a newly renovated pool, expansive deck, and landscaped grounds.

Orangeville 3BDRM House

This home can accommodate an escape from the city to relax/explore or offer a quiet place to work or recharge if on a business trip. This clean & cozy townhouse is perfect for the whole family. Enjoy a full kitchen stocked with coffee, sugar, honey & spices. The dining area sits 4 with some bonus additional seating at the nearby island. The living room has a large couch with 2 additional seating options that have a clear view of the television. There are 3 fantastic spacious bedrooms.

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!

Stylish 3 Bedroom Getaway in Orangeville

Nestled among tree sculptures and lakes, just steps away from downtown and minutes from the serene beauty of Island Lake Conservation Area. Our urban oasis is complete with a comfortable bed, fully equipped kitchen, chic living area, and private balconies. Be transported through time as you wander the streets of downtown, admiring vintage architecture and vibrant culture. Experience the magic of nature and city living combined in one unforgettable stay!

Charming Log Home - 25 private acres in Caledon

Our home sits on the rolling hills of Caledon East surrounded by a serine ambiance of pure peace and quiet. Just 45 minutes from the GTA where you can make memories w/family and friends. Take a walk though the trails, enjoy sitting by the pond, or enjoy skating or snow shoeing during the winter months. We welcome all our guest(s) to take a deep breath, inhale peace and exhale happiness.

The Coastal Cottage

Escape to our modern bohemian beachfront cottage for a serene and stylish getaway. Whether you're seeking a romantic retreat or a peaceful solo adventure, our little slice of paradise is the perfect backdrop for creating lasting memories. Book your stay today and start counting down the days until you wake up to the sound of crashing waves and breathtaking sunrises. t4yh7

Lake Simcoe Cottage | Hot Tub, Dock, Games &Kayaks

Welcome to Lake Simcoe Beach House! Escape to a peaceful lakefront retreat designed for families and groups seeking comfort and adventure in every season. Located on the pristine shores of Lake Simcoe, this spacious home offers breathtaking sunsets, sandy-bottom waters safe for swimming, and an array of indoor and outdoor activities for an unforgettable getaway.