Vacation rentals in Caledon

A bright & chic 2 bedroom urban apartment

Come & relax...in privacy. "The Cooper" is an 833 square foot 2 bedroom that is unique & intimate. You will be on the main floor of this bungalow, with a basement apartment below you. The kitchen is amazing, complete with gas range & dishwasher. Primary bedroom has in-suite laundry, & the elegant bathroom has heated floors! Exclusive entrance and private outdoor area with BBQ. Parking out front. A short hop from Toronto, Dufferin County has all you need for a relaxing getaway! Come & See :)

Country Getaway in Erin

Forget all your worries in this private country retreat. Stay in our 2 storey private apartment located on a 38 acre lot, where peace and tranquility are at your doorstep. Enjoy long walks along tree-lined roads with picturesque views and perfect star gazing at night. Comfortable accommodations up to 4 with 1.5 bathrooms, and your own fully functional kitchen. Only 3 minutes from town where you can enjoy some good country hospitality. Coffee shop, bakery, ice cream shop and much more await you.

Tamarack Trails Wilderness Cabin

Welcome to Tamarack Trails – your peaceful escape nestled in a quiet forest. This luxury cabin offers the perfect blend of comfort and nature, surrounded by 40 acres of unspoiled wilderness. Drift off to sleep in a cosy queen-sized bed and wake to the sound of song sparrows. Soak in a relaxing tub as you gaze out floor-to-ceiling windows. Enjoy breakfast on your private deck. Spend your days wandering private trails with stunning scenery or snowshoe through snow-draped white pines in winter.

Hockley Haven

Kick back and relax in this calm, stylish space. Newly renovated cozy 1 bedroom carriage house loft (appx 650 sq ft) above detached 3 bay garage in serene country setting on 5 acres of pine and cedar with a river running thru it. Pullout couch can accommodate 2 additional people. Walk across the road to Pollinator Garden & Island Lake Trails. 6 min drive to Hockley Valley Resort and Adamo Estate Winery, as well as beautiful downtown Orangeville boasting fabulous restaurants and quaint shops.

The Clayhill Bunkie

Looking for a place to get away that’s semi off-grid or a place that’s kind of like glamping? On The Bruce Trail and minutes from Silvercreek & Terra Cotta Cons. areas, the Credit River, the villages of Glen Williams &Terra Cotta, &the town of Georgetown. Spend your day hiking, cycling, antique hunting, tubing, or site seeing, then order in or grab take-out and come relax by a roaring fire. Firewood is included, adding great value to your stay. You WILL hear wildlife and farm animals here.

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!

Separate apartment with pool, on golf course.

Enjoy a newly renovated studio apartment with a private entrance and exclusive access to a serene inground pool. This cozy space is furnished with Restoration Hardware pieces and features a fully equipped kitchen, high-speed WiFi, and a patio with an outdoor barbecue—perfect for remote workers or a peaceful getaway. Situated behind Caledon Woods Golf Course, it’s just 7 minutes from the Caledon Equestrian Park, 30 minutes from Pearson Airport, and close to highways leading to Toronto.

Hockley Valley Cozy Cottage

Take it easy at this unique and tranquil setting where the entire property is yours! Freshly renovated cottage only 600M from Hockley Valley Resort and also close to restaurants and hiking trails. This cottage sleeps 4 comfortably with separate bedroom. Picturesque setting directly on Nottawasaga river with mature gardens and plenty of outdoor space. Morning coffee or afternoon drinks under the covered gazebo at the waters edge or relax in the hammocks, this place truly has it all.

Luxury tiny home on peaceful country estate

Escape to Heirloom Tiny Home - where macro luxury meets a micro footprint. Nestled on 23 peaceful acres, surrounded by aspen and pine forests, just 10 minutes from the picturesque town of Elora. Wake up to serene pond views as horses and sheep graze in your view. Organic linens, artisanal soaps, and a spa-like bathroom soothe the senses. Cozy up by the indoor fire and gaze at the stars. Enjoy fine dining at the Elora Mill and Spa, enjoy popular shops or hike the Elora Gorge nearby.

Cheerful Private Studio House

Bring yourself to this excellent place for a peaceful family-friendly stay. The Place is near YYZ Toronto Airport, the Go Train station for downtown Toronto, and walking to food outlets, Cassie Campbell Community Centre. Our Place is highly sought-after and has top-rated reviews by our guests. The place is warm and well-lit to provide you cozy comfortable stay. Ensuite private bathroom, walk-in closet, modern kitchenette with dining island space. spacious exercise and yoga area.

Sweet Studio Cottage Cozy Fireplace Backyard Haven

Experience a private, urban studio cottage located in a gorgeous tree-filled backyard in the Junction neighbourhood, close to downtown Guelph, with full amenities. Comfortable queen bed, natural gas fireplace, fully stocked kitchen, separate shower, 2-piece washroom, additional sleeping loft, private back flagstone patio, and sauna. Located in the heart of the Junction Village intentional community, guests can connect with others, or have a private retreat experience.

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!