Pet-friendly holiday rentals in Caledon

4.99 out of 5 average rating, 403 reviews

A charming stone house is set against a backdrop of lush greenery. The facade features large windows and a welcoming porch. A well-kept lawn leads to the entrance, offering a serene view of the surrounding trees.

Cabin in Arthur

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

Tiny home in The Junction

A stone pathway leads to the exterior of a small wooden cabin, surrounded by lush greenery. Hanging flower baskets adorn the walls, and a tranquil water feature can be seen nearby. The natural scenery creates a peaceful atmosphere, inviting exploration.

4.99 out of 5 average rating, 177 reviews

Tranquil Tiny House Retreat 4-Season Radiant Floor

Take it easy at this unique cabin experience in the city. The Tiny House is a private 9’ x 12’, fully insulated, 4 season cabin with a couch, kitchenette with running water, queen bed, Loftnet hammock & outdoor shower. Enjoy the natural beauty of our half acre tree-filled backyard, yet still close to downtown Guelph. This is a glamping experience that requires appreciation for tiny house living. Guests have access to a separate portable washroom, by walking about 100ft to the back of the yard.

4.98 out of 5 average rating, 266 reviews

The exterior of the guest house features a wrap-around composite deck with glass railing, overlooking the direct waterfront views of Lake Ontario. The structure is surrounded by lush greenery and is complemented by large windows allowing natural light into the living space.

Guesthouse in Lincoln

Cottage On Lake Ontario Niagara

OPEN TIMESLOTS DECEMBER 10-12 (2 nights/3 days) DECEMBER 15-18 (3 nights/4 days) Unwind at our cozy guest house. Beautiful 2-bedroom cottage. Enjoy the direct waterfront views from the living room, bedroom and wrap around composite deck. Outdoor fire pit and BBQ. We are located along the south shore of Lake Ontario amongst the fruit belt of the Niagara. Set in vineyards, peach, nectarine and plums. Close to wineries & shops. Free Tesla charging. Views from the cottage include: Lake & orchards.

Guesthouse in Halton Hills

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.

4.92 out of 5 average rating, 158 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? 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.

4.97 out of 5 average rating, 112 reviews

Home in Alton

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

4.98 out of 5 average rating, 260 reviews

A spacious living area features a variety of seating options, including a cozy couch and rocking chairs. Large windows allow natural light to enter, illuminating the lush indoor plants. Decorative rugs and artwork add character to the eclectic decor, creating a relaxed atmosphere.

Farm stay in Uxbridge

Private Loft w Sauna, Fireplace, Wi-Fi & Projector

Welcome to the LOFT - A private, eclectically designed spa-inspired unique stay in the historic Webb Schoolhouse, less than an hour from Toronto. Featured in TORONTO LIFE in 2021, this private loft includes a sauna, unique hanging bed, wood stove, kitchenette and is filled with art, and huge tropical plants as well as a projector & giant screen for epic movie nights. Relax and recharge, roam the grounds and enjoy the beautiful outdoor spaces, the permaculture farm, animals, and fire pit.

4.86 out of 5 average rating, 162 reviews

Home in Caledon

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!

4.91 out of 5 average rating, 531 reviews

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

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. The Suite is located on the same property as our farmhouse, Country Cabin and Event Barn. Blinds are provided to enhance your privacy during your stay. The Suite includes a full kitchen, king sized bed, propane BBQ and many other amenities, for a full list please review the "What this place offers" section of our listing.

4.91 out of 5 average rating, 463 reviews

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

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!

4.96 out of 5 average rating, 138 reviews

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

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.

4.98 out of 5 average rating, 295 reviews

A rustic living area features exposed wooden beams and a stone fireplace, providing a cozy focal point. Comfortable seating options include an armchair and a sofa arranged around a wooden coffee table. Large windows allow natural light to illuminate the space.

Guest suite in Mono

Mono - Charming, Rustic 150 Year Carriage House

This rustic space is perfect for a weekend getaway, year round. Close to ski hills, nature trails and the quaint town of Orangeville the Carriage house will provide you the authentic feel of our iconic cabin in the woods with the sophistication and comforts of your personal retreat for the weekend. The interior design is eclectic, funky and perfectly contrasts the rustic charm of the 140 year old, hand cut wooden beams and the overall log cabin environment.

Guest suite in Orangeville

A cozy living area features a light-colored sofa with decorative cushions, a coffee table, and a wall-mounted television. A slim electric fireplace is situated beneath the TV. To the rear, a fully equipped kitchen can be seen, enhancing the space's functionality.

5 out of 5 average rating, 176 reviews

Garden Studio Apartment

Enjoy a stylish experience at this centrally located place. Newly renovated 1 bdrm walkout apartment located in our home in downtown Orangeville. Steps to Theatre Orangeville, Orangeville farmers market, and Jazz & Blues Festival. Enjoy evenings on your own patio in a 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.

Popular amenities for Caledon pet-friendly home rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.94 out of 5 average rating, 324 reviews

A modern dining area features a wooden table set for a meal, surrounded by light-colored chairs. A large window on the wall allows natural light to brighten the space, showcasing a view of greenery. The adjoining kitchen is visible in the background.

Home in Paris

The Walnut - Steps to Canoe Launch & Downtown

4.71 out of 5 average rating, 41 reviews

A covered hot tub area features wooden paneling and a vaulted ceiling with skylights, allowing natural light to fill the space. The hot tub, surrounded by stone tiles, creates a tranquil environment for relaxation, providing views of the greenery outside through large windows.

Home in Caledon Village

Charming and Peaceful Retreat with Hot Tub

4.99 out of 5 average rating, 161 reviews

The serene backyard features a heated saltwater pool surrounded by a stone deck, bordered by lush greenery and blooming trees. A patio area includes outdoor seating and a grill, while large windows overlook the pool, enhancing natural light in the adjacent indoor space.

Home in The Beaches

Year-Round Heated Pool & Hot Tub Family Oasis

4.99 out of 5 average rating, 137 reviews

The exterior of the cottage is shown, featuring a combination of wood and stone textures. Wide porches wrap around the entrance, while large windows provide natural light. Snow lightly covers the ground, enhancing the peaceful countryside setting, with scattered trees visible in the background.

Home in Brantford

Langford House

4.97 out of 5 average rating, 126 reviews

A spacious deck is showcased at night, featuring warm lighting that highlights its structure. An in-ground seating area with surrounding lights creates an inviting atmosphere. The surrounding landscape is visible in the background, providing a serene backdrop.

Home in Kitchener

RivertrailRetreat | Unique Deck + Skiing + Theatre

4.94 out of 5 average rating, 139 reviews

An open concept game room features a polished pool table at the center, with a bar area equipped with stools to one side. Large windows allow natural light to fill the space, while a mounted TV and comfortable sectional couch create an inviting entertainment area.

Home in Badjeros

JJ’s small town country retreat

4.94 out of 5 average rating, 133 reviews

A private outdoor space is highlighted by a spacious hot tub surrounded by wooden decking. Nearby, two red Adirondack chairs invite relaxation. Lush greenery and trees provide a natural backdrop, creating a serene environment ideal for unwinding.

Home in St. Catharines

Niagara Wine Country Art House | Hot Tub | 2 ppl

4.91 out of 5 average rating, 116 reviews

A modern two-story house is set against a green backdrop, featuring large windows that allow natural light to flood the interiors. The driveway leads to an attached garage, while a neatly maintained lawn surrounds the property, enhancing its curb appeal.

Home in West Oakville

Large Luxury Villa with Swim Spa! Near downtown!

Pet-friendly home rentals with a pool

4.9 out of 5 average rating, 243 reviews

Cottage in Alcona

Utopia villa and spa

Condo in Humber Bay Shores

A spacious living area is featured, with large windows offering natural light and views of the city. A comfortable gray sofa is situated alongside a vibrant red armchair. A wooden coffee table rests on a patterned rug, complemented by a flat-screen TV and decorative artwork.

4.8 out of 5 average rating, 111 reviews

Humber Bay Family Friendly condo w Terrace&Parking

4.94 out of 5 average rating, 124 reviews

The living area features modern furniture with a blue sofa and a wooden coffee table. A piece of wall art depicting floral arrangements is displayed above the sofa. Large windows allow ample natural light and showcase city views.

Condo in Kitchener

Hydropool Spa HotTub/Bowling Alley/Patio/BBQ/Games

Guest suite in Orangeville

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.

4.96 out of 5 average rating, 171 reviews

Your Peaceful Santuary in Nature

4.95 out of 5 average rating, 233 reviews

The interior features rustic log walls complemented by wooden beams. A dining area is set with a white tablecloth and dark chairs, while a vintage dresser holds decorative items. A minimalist wall art piece depicting a deer adds character to the warm space.

Guest suite in Uxbridge

Mackenzie Cottage

4.85 out of 5 average rating, 144 reviews

A private backyard space features a swimming pool with steps leading in. Comfortable lounge chairs sit nearby on the concrete patio, while vibrant green trees and a well-maintained lawn surround the area. A shaded seating area can be seen in the background.

Home in Waterloo

Entire Guest Unit+Free Parking by Glenbridge Plaza

Guesthouse in Orangeville

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.

4.96 out of 5 average rating, 378 reviews

Sunny Pines Farm Studio Tennis Court/Bruce Trail

Condo in Entertainment District

A modern living area features a grey sectional sofa paired with a wooden coffee table. Natural light streams through large windows, revealing a view of the city. A 55-inch Smart TV is positioned on a dark wood console, complemented by decorative elements on the table.

4.93 out of 5 average rating, 121 reviews

Charming Condo w Parking, CN Tower View & Pool

Private, pet-friendly home rentals

5 out of 5 average rating, 56 reviews

A hand-crafted cabin features a dark exterior with bright wooden accents, surrounded by tall trees. A welcoming porch includes a small table and chairs, extending towards a natural landscape covered in wood chips.

Cabin in Guelph-Eramosa

Fern Hill Cabin

5 out of 5 average rating, 39 reviews

A modern kitchen area is visible, featuring white cabinetry and stainless steel appliances. A rustic barn door opens to the bedroom. The dining space includes a dark wood table surrounded by four chairs, complemented by a cozy sofa adorned with colorful cushions.

Guesthouse in Brampton

Private & Detached Downtown Brampton Garden Suite

Tiny home in Horning's Mills

A wooden bunkie is set among tall trees, featuring a spacious deck surrounded by a railing. A barbecue unit is positioned on the deck, and a rustic charm is evident in the structure with its natural wood finish and a sloped roof.

4.91 out of 5 average rating, 182 reviews

Pine River Bunkies: Owl’s Roost Off Grid Cabin

4.83 out of 5 average rating, 75 reviews

Cabin in New Tecumseth

Romantic Spa/Sauna Cabin Getaway

4.97 out of 5 average rating, 105 reviews

The Lodge is surrounded by lush greenery and features a wraparound deck with outdoor seating. A gentle stream flows nearby, accentuating the natural landscape. The rustic exterior blends seamlessly with the forested backdrop, providing a peaceful and private retreat.

Chalet in Markdale

Grey Highlands Lodge

4.79 out of 5 average rating, 28 reviews

A cozy studio space features a spacious bed with a white comforter and blue accent pillows. The kitchenette is visible in the background, equipped with white cabinets and modern appliances. A tray with two glasses and a bottle of wine rests on the bed, enhancing the welcoming vibe.

Home in Caledon

Live Lavishly: Modern Studio, 5G, Parking

5 out of 5 average rating, 22 reviews

A serene scene at dusk captures three animals, including a cow and two horses, walking along a path in a pasture. Sunlight filters through trees in the background, creating a warm glow over the landscape.

Farm stay in Orangeville

3 separate sleeping rooms on 23-acre horse farm