Pet-friendly holiday rentals in Caledon

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, 382 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.

4.99 out of 5 average rating, 412 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

4.87 out of 5 average rating, 223 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!

4.9 out of 5 average rating, 513 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

Cabin stay and play! 10 mins to Canadian Open!

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!

4.97 out of 5 average rating, 297 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 MAY 5 (tonight) MAY 16-31 JUNE 1-30 JULY 1-31 Please mark this listing as a favourite to get notifications of last minute deals. 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. Set in vineyards, peach, nectarine and plums. Close to wineries & shops. Free Tesla charging. Views from the cottage include: lakefront and orchards.

4.98 out of 5 average rating, 121 reviews

The exterior of a two-story house showcases a blend of stone and dark wood siding, with a spacious deck accessible from the upper floor. Lush green grass and neatly arranged flower beds surround the home, while a gray sky sets a calm backdrop.

Home in Alton

Cozy Country Spring Getaway | HotTub + Fire Pit

Escape to the countryside this spring 🌸 Unwind in the hot tub or pool, enjoy cozy fires under the stars, and soak in the peaceful charm of Alton. 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

4.96 out of 5 average rating, 146 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.

4.95 out of 5 average rating, 170 reviews

Dome in Zephyr

Glass Dome - Sleep Under The Stars- Free Sundays

Discover this new, stunning 22ft Glass Geodesic Dome nestled in the heart of Uxbridge. Imagine waking up surrounded by 360-degree panoramic views of the natural landscape Please note... its FULL WEEKEND STAYS ONLY - BOOK FRIDAY AND SATURDAY-SUNDAY IS FREE. This allows guests to fully enjoy their Sunday without feeling rushed to check out at 11am. Enjoy all day Sunday with option of staying the evening. 8X12 BUNKIE NOW AVAIL. SLEEPS 4 ( 2 bunk beds)

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, 195 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.

4.99 out of 5 average rating, 192 reviews

A unique double A-frame house is framed by lush greenery, with a spacious driveway leading to the entrance. The structure features a combination of wood and stone elements, while flower beds with emerging blooms add color to the natural surroundings.

Cottage in St. Jacobs

St. Jacobs Triangle House - Countryside Escape

Welcome to Triangle House, a unique double A-frame situated on a private 1.7 acre lot, fronting on the Conestogo river Only 6 minutes drive from St.Jacobs center, 1.5 hours drive from Toronto, 15 minutes drive from the University of Waterloo and 25 minutes to Elora. Bring the whole family. This 3 bed, 3 bath home comfortably sleeps 6. Soak in the countryside from the sprawling deck and grounds, while enjoying all the comforts of a modern home.

4.93 out of 5 average rating, 214 reviews

Two brown horses are depicted in a snow-covered outdoor setting, closely positioned with their noses touching. Flakes of snow gently fall around them, creating a serene winter scene, while a house and snow-covered trees are subtly blurred in the background.

Bungalow in Hamilton

Horse Ranch with Hot tub

Your very own house with lots of open space outdoors. Equipped with wifi and many home comforts. Enjoy taking a dip in the Hot tub, feeding and petting horses, walking forest trails, BBQ, have a picnic for lunch. Options are limitless to spend your time in the country and take a break from the city life. Relax with whole family or friends at this peaceful place to stay!

4.85 out of 5 average rating, 151 reviews

A charming wooden Bunkie is nestled among lush greenery. The front porch features a small wooden deck with two red chairs and a round table. Large windows allow natural light to illuminate the interior while the door is framed by a welcoming entry.

Cabin in Caledon East

Bunkie in the Forest (Heated)

Welcome to Bunkie in the Forest. We are a fully insulated and heated Bunkie. The perfect place if you want to relax, recharge, have some fun while exploring our property in the forest, hiking nearby trails or enjoying the beauty of nature. Our Bunkie is perfect for 2 people. It is comfortable and cozy, it is everything you want for a perfect weekend getaway!

Popular amenities for Caledon pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.94 out of 5 average rating, 339 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

4.96 out of 5 average rating, 315 reviews

Home in Port Dalhousie

Lux Lake Ont Beachfront - Fire Pit & Sunset Views

4.87 out of 5 average rating, 253 reviews

Home in Youngstown

Lake Ontario Home+Hot Tub, sleeps 10 | Tucked Away

4.96 out of 5 average rating, 145 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

4.98 out of 5 average rating, 153 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

4.93 out of 5 average rating, 165 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

4.86 out of 5 average rating, 126 reviews

A warm living area features a large leather sofa paired with a circular chair. A rustic wooden coffee table is positioned in front. Natural light filters through sheer curtains, illuminating the space with a cozy ambiance. A wood-burning fireplace is framed by vertical wood paneling.

Home in Pickering

Cosy 3-Bedroom Home in Quiet Cul-de-Sac.

Home in Niagara-on-the-Lake

A serene view of lush greenery features a winding stone path leading towards the sparkling waters of the Niagara River. Tall trees cast gentle shadows over the expansive grassy area, creating a peaceful outdoor atmosphere.

4.96 out of 5 average rating, 126 reviews

🥂Breathtaking Views of the Niagara River

Pet-friendly home rentals with a pool

Villa in Niagara-on-the-Lake

4.86 out of 5 average rating, 157 reviews

Wine Country Villa with Private Pool

4.91 out of 5 average rating, 107 reviews

A bright sunroom is showcased with a glass ceiling and walls, providing expansive views of the surrounding nature. A glass dining table is surrounded by black chairs, resting on a soft area rug. The space offers a connection to the outdoors while remaining sheltered.

Home in Rouge

Ravine Paradise ! heated pool and hot tub!

5 out of 5 average rating, 131 reviews

Condo in Innisfil

Oasis Spa w/ Private Sauna!

4.91 out of 5 average rating, 140 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

Resort Condo with Bowling and Spa Hot Tub

4.84 out of 5 average rating, 170 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

4.97 out of 5 average rating, 203 reviews

Guesthouse in Breslau

House on the Hill

Home in Niagara-on-the-Lake

A private pool is surrounded by a secure fence, featuring a concrete deck with steps leading into the water. Comfortable lounge chairs are positioned nearby, set against a backdrop of lush greenery and a clear blue sky.

4.9 out of 5 average rating, 105 reviews

Wine country Cottage 15 min drive to old Town NOTL

4.99 out of 5 average rating, 102 reviews

Apartment in Waterloo

Charming Hideaway: 1-bedroom Apartment

Private, pet-friendly home rentals

4.91 out of 5 average rating, 54 reviews

An outdoor seating area features a gazebo with comfortable seating and a decorative rug. The surrounding garden showcases various plants and flowers, alongside a pathway leading to the guest home. The structure is nestled among trees, contributing to a serene setting.

Guesthouse in Mono

Mono Countryside Home & Farm

4.99 out of 5 average rating, 73 reviews

A cozy living area features a stone fireplace with a warm fire, surrounded by comfortable seating in various patterns and colors. A wooden coffee table sits at the center, and a piece of artwork depicting a winter scene hangs above the mantel.

Home in Erin

Stonewell Farm Guest House

5 out of 5 average rating, 78 reviews

Cabin in Guelph-Eramosa

Fern Hill Cabin

4.73 out of 5 average rating, 56 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

4.91 out of 5 average rating, 58 reviews

Home in Brampton

The Urban Nest

4.89 out of 5 average rating, 203 reviews

Large glass patio doors frame a scenic view of the waterfront, revealing a private deck with seating and a hot tub surrounded by trees. Sunlight casts a warm glow over the area, enhancing the sense of tranquility.

Cottage in Innisfil

Stunning Lakefront Cottage Hot Tub & Sauna

4.94 out of 5 average rating, 16 reviews

An aerial view showcases a cozy country home surrounded by vibrant autumn foliage. Various trees display shades of green, orange, and red. Beneath the house, a circular patio area can be seen, bordered by a well-maintained lawn, while a winding road leads up to the property.

Bungalow in Caledon East

Caledon Country Charm