Pet-friendly vacation rentals in Caledon

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Top-rated pet-friendly home rentals in Caledon

Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

An open bedroom features a spacious bed with crisp white linens, set against a large window. The window offers a cozy view of a softly illuminated outdoor setting, with string lights glowing in the evening. Warmth is provided by a wall-mounted air conditioner.

Guest suite in Schomberg

4.92 out of 5 average rating, 508 reviews

Romantic King Suite | Countryside | Pet Friendly

Escape to Our Cozy Country Suite – your perfect getaway on a peaceful, picturesque farm. Ideal for a romantic escape or quiet retreat, just 50 minutes from Toronto. This private suite, attached to our farmhouse with its own entrance, includes everything you need to relax: ✨ Full kitchen 📶 WiFi 📺 55” 4K Smart TV 🛁 Modern 3-piece bathroom 🧺 In-suite laundry 🔥 Propane BBQ (tank, tongs, flipper provided) Unwind by the propane fire pit or explore scenic walking trails right outside your door.

Guest favorite

An outdoor pool area features a surrounding deck with wooden steps leading up to it. Bright blue water reflects the sky, and vibrant green grass borders the patio. Two red Adirondack chairs are placed nearby, complemented by lush trees and a distant green landscape.

Guesthouse in Orangeville

4.95 out of 5 average rating, 361 reviews

Sunny Pines Farm Studio Tennis Court/Bruce Trail

Perfect for a getaway in the country. A bright, spacious, open-concept designer studio featuring beautiful rolling-hill vistas, queen bed, 3-piece bathroom, dedicated bbq, heat/AC plus a wood burning stove, wet bar with a Nespresso machine, deluxe counter-top oven & bar fridge and all new tennis court, laundry available upon request. Mono Cliffs, Boyne Valley, Hockley Valley Nature Reserve Prov. Parks & Mansfield Recreation Centre are minutes away. Ideal hiking, cycling, snowshoeing and xcsking.

Top guest favorite

Cabin in Arthur

4.98 out of 5 average rating, 381 reviews

The Stone Heron

Welcome to the Stone Heron, a diamond in the country side! An hour from Toronto.Check out our insta-gram :thestoneheron. Small stone house completely reno'd!Large master bedroom, gorgeous bathroom 2nd BR bunk beds w/game table downstairs a pool table & darts. DVD, TV wii. Entire home is yours to use, its private, nestled into a hillside covered in periwinkle -nature your only neighbour! Large pond walking trails, wildlife, unplug relax and enjoy!Star filled nights amazing sunsets. Pet friendly

Guest favorite

A charming exterior of the Clayhill Bunkie is presented, featuring a dark blue wooden facade with a steeply pitched roof. Two windows, adorned with flower boxes, flank a central door that is decorated with a natural wreath. Lush greenery surrounds the entrance, enhancing the serene setting.

Guesthouse in Halton Hills

4.93 out of 5 average rating, 122 reviews

The Clayhill Bunkie

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

Guest favorite

An inviting outdoor space features a wooden pergola with string lights, surrounding a dining table and seating area. A private hot tub is positioned nearby, with lush greenery and vibrant flower arrangements enhancing the serene environment.

Cabin in Erin

4.91 out of 5 average rating, 424 reviews

Erin Cabin Getaway and Bunkie

Take it easy at this unique and tranquil getaway. Located steps from Calerin Golf Course (350 m) and includes many amenities, such as: a BBQ, patio w/ dining area, private hot tub, acres of groomed trails, games galore, pool table, fire pit, comfy queen bed w/ separate heated bunkie with a second queen bed and more! Optional pull out available, please inquire within (fee may apply). 2 km or 5 mins, from the picturesque town of Erin. Lots of restaurants, shops, and plenty to do!

Guest favorite

A cozy cabin is framed by tall green trees, reflected in the calm water of a private pond. Outdoor seating in vibrant red adds a pop of color, enhancing the serene natural setting.

Cabin in Mono

4.96 out of 5 average rating, 650 reviews

Mono — Cabin in the Woods Experience

This cozy cabin in the woods is perfect for content creation, photography, proposals or just enjoying nature and swimming in the summer or ice skating throughout the winter. Only minutes from Orangeville, Hockley Valley and less than one hour from downtown Toronto you feel hours away from everything. Swim in your private pond, recharge and escape the noise of the city and relax in your own personal paradise! Cabinonthe9 is one of Canada's top short term rental destinations.

Top guest favorite

A cozy studio space features high ceilings with exposed wooden beams and a bright, airy atmosphere. A double bed is adorned with a soft blanket, while a seating area with a rattan chair and small sofa invites relaxation. Natural light flows through large windows, illuminating the room.

Guesthouse in Guelph

4.9 out of 5 average rating, 559 reviews

Beautiful Studio Cottage • Urban Retreat Guelph

Experience an independent, private, sparkling clean studio close to downtown Guelph with full amenities. Located in a gorgeous tree-filled 200 ft backyard, this cozy urban cottage has a comfortable double bed with new mattress, gas fireplace, fully stocked kitchen, separate shower, 2-piece washroom, sleeping loft, and private back patio. Located in the heart of the Junction Village intentional community, guests can connect with others, or have a private retreat experience.

Superhost

A glamping dome is set amidst a lush green landscape, reflected in a serene pond featuring lily pads and blooming flowers. Towering trees provide a natural backdrop, while a wooden deck extends from the dome, enhancing the outdoor experience.

Dome in East Gwillimbury

4.9 out of 5 average rating, 234 reviews

Deerleap Glamping Dome

Located close to the city, our four-season glamping dome offers a peaceful and unique escape. In winter, the snow-covered landscape creates a magical scene, while inside, the wood pellet stove keeps the dome exceptionally warm and cozy. Nestled on 10 acres of picturesque land and a stunning pond view, Enjoy everything you need—from upscale sanitary facilities to fast Wi-Fi. Whether you’re celebrating a birthday, an anniversary, or simply seeking quiet time in nature.

Top guest favorite

A cozy sitting area is presented with a blue checkered sofa and a striped armchair, adorned with nautical-themed cushions. Light is provided by two lamps on either side, illuminating the artwork and rustic wooden beams above.

Guesthouse in Erin

4.98 out of 5 average rating, 126 reviews

The Captain's Cottage at Willow Pond

You will have your own private one bedroom cottage on our 17 acre property. Your countryside getaway can be as quiet or as busy as you make it. You will have access to our tennis court, swimming pool, hot tub, gazebo, pond, garden and woodland trails. Adults are welcome to use the exercise studio. There is a flock of heritage chickens, guinea hens and quail who lay beautiful eggs for your breakfast. We also have bees who produce delicious honey for our guests.

Top guest favorite

A charming entrance is framed by an inviting covered porch, featuring decorative woodwork and a bright yellow door. Lush greenery surrounds the entryway, providing a serene and welcoming atmosphere. A stone path leads toward the door, enhancing the home's inviting character.

Home in Elora

4.96 out of 5 average rating, 782 reviews

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.

Top guest favorite

A modern living space is presented, featuring a wall-mounted flat-screen TV above a cozy electric fireplace. A patterned armchair and a wooden coffee table are positioned on a soft area rug. Light-colored walls and bright overhead lighting create an inviting atmosphere.

Guest suite in Orangeville

5 out of 5 average rating, 151 reviews

Garden Studio Apartment

Enjoy a stylish experience at this centrally located place. Newly renovated 1 bdrm apartment located downtown Orangeville. Steps to Theatre Orangeville, Orangeville farmers market, and Jazz & Blues Festival. Enjoy evenings on your own private backyard overlooking the garden. Enjoy walks on the Island lake Conservation Park.. Dine at any of the many fine restaurants or cook at meal in your own fully equipped kitchen.

Guest favorite

A serene winter scene captures a snowy landscape framed by tall evergreen trees. A clear blue sky contrasts with the bright white snow covering the ground and adjacent areas. The pathway leads towards a structure partly obscured by the snow-laden trees, suggesting a peaceful retreat.

Guest suite in Orangeville

4.96 out of 5 average rating, 163 reviews

Your Peaceful Santuary in Nature

Tranquil space to go walking through the 20 acres of forest with trails, lots of wildlife, and beautiful bright stars at night for stargazers. You can have a coffee in the morning on the patio set in front of the suite and have a drink on one of the hills in comfortable muskoka chairs up on a hill of the property and watch the sunset or sunrise if you are an early bird.