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Vacation rentals in Caledon

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Top-rated vacation rentals in Caledon

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
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
4.99 out of 5 average rating, 411 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 spacious glamping dome is nestled among lush green trees, showcasing large windows and a triangular design. The entrance is framed by rustic outdoor seating, and soft lighting emanates from inside, creating an inviting atmosphere amidst the surrounding foliage.
Dome in Utopia
4.95 out of 5 average rating, 265 reviews

Off-grid Glamping Dome Nestled in the Woods

Welcome to our private campsite in Utopia, ON. Our family’s glamping dome is your chance to experience a unique getaway surrounded by the sights & sounds of nature. Amenities include camping essentials & some glamping perks: king size bed, bbq, fireplace, Indoor incineration toilet, soap & water, outdoor shower (summer only), kettle, cooking utensils. Nearby is Purple Hill Lavender Farms, Drysdale's Tree Farm, Tiffin Conservation Area, Nottawasaga & golf courses. Wasaga Beach is 30 min away.

Guest favorite
Home in Caledon
4.87 out of 5 average rating, 216 reviews

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!

Top 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, 175 reviews

The Clayhill Bunkie

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

Top guest favorite
The modern tiny home features a black exterior and a large glass front, allowing natural light to illuminate the interior. A simple outdoor seating area with two chairs is visible, surrounded by lush greenery and trees, creating a connection with the serene natural surroundings.
Tiny home in Arthur
4.97 out of 5 average rating, 372 reviews

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.

Superhost
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
4.9 out of 5 average rating, 510 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!

Top guest favorite
A spacious living area features a blue sofa with a light throw, positioned beside a circular coffee table. Wall art adorns the white walls, and natural light filters through a decorative window. A white cabinet and a small plant complete the cozy atmosphere.
Loft in Mono
4.98 out of 5 average rating, 163 reviews

Hockley Haven

Kick back and relax in this calm, stylish space. 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.

Guest favorite
The geodesic dome features a modern white exterior, set against a backdrop of trees. A wooden deck extends from the dome, leading to a covered gazebo, with a pathway of wood chips guiding the approach. Soft sunlight filters through the branches, creating a serene atmosphere.
Dome in Uxbridge
4.84 out of 5 average rating, 102 reviews

The Bubble Glamping Dome

Escape to a luxury geodesic dome on our scenic farm, nestled at the edge of the forest. Fully equipped with heating, cooling, a private washroom, deck, and hot tub, it’s the perfect blend of comfort and nature. Explore the farm, meet our sheep, chickens, and livestock guardian dog, or hike over 100 acres of connected regional forest. Whether you’re relaxing under the stars or adventuring outdoors, this unique glamping retreat promises an unforgettable experience.

Top guest favorite
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.
Guest suite in Orangeville
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.

Top guest favorite
A private detached apartment is visible nestled among tall trees and lush greenery. The wooden exterior of the structure blends harmoniously with the natural surroundings. A pathway leads towards the entrance, framed by a vibrant landscape of ferns and colorful shrubs.
Guest suite in Caledon
4.99 out of 5 average rating, 145 reviews

Casa Caledon-Secluded Suite Surrounded by Nature

Take it easy at this unique and tranquil getaway on 3 acres of land The suite is close to conservation areas Cheltenham Badlands, Fork of the Credit and Terra Cotta Bruce trail, golf courses, restaurants, bakeries, butchers, farm produce and city needs are close Each season is wonderful Spring/summer has lush forests, the pond and fire pit Fall walks with the beautiful colours Winter has a white blanket and access to winter sports

Top guest favorite
An outdoor fire pit surrounded by gravel is present, featuring two wooden chairs. A hot tub is located nearby, positioned in front of a geodesic dome with large windows. String lights are draped overhead, illuminating the outdoor space.
Dome in Utopia
4.96 out of 5 average rating, 170 reviews

Glamping Dome Riverview Utopia

Come retreat into nature at the Riverview Glamping Dome… a 4 season getaway located on Rustic Roots Farm and Eco-retreat 1 hour north of Toronto. Whether you're looking for a romantic getaway or to come disconnect from the hustle and bustle of everyday life this geodesic dome is for you! Located on 64 sprawling acres come explore hiking trails, go fishing, relax in the hot tub, and stargaze fireside.

Top guest favorite
Two green Adirondack chairs, positioned facing the lake, are placed on a spacious deck with a red side table nearby. Lush greenery surrounds the water, reflecting the serene clouds above, while residential homes line the opposite shore.
Guest suite in Brampton
4.93 out of 5 average rating, 147 reviews

Lakeside Unit & Breathtaking View! 15 Mins to YYZ!

Scenic lakeside walkout basement apartment with breathtaking view! Bright, clean and spacious. Full kitchen, washer and dryer for your convenience. Free WiFi and one parking. Located at the most prestigious area in Brampton - Professor's Lake. Out side of my house is a trail around the whole lake for around 3 kilometers. Wonderful for runners or simply walk around the lake to enjoy the nature.

Popular amenities for Caledon vacation rentals

When is the best time to visit Caledon?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$14,436 GYDG$14,436 GYDG$14,227 GYDG$14,854 GYDG$15,273 GYDG$16,737 GYDG$16,528 GYDG$17,156 GYDG$15,900 GYDG$15,482 GYDG$14,854 GYDG$14,854 GYD
Avg. temp-7°C-6°C-1°C6°C12°C17°C20°C19°C15°C9°C3°C-3°C

Frequently Asked Questions

  • Are there family-friendly vacation rentals in Caledon?

    Caledon has more than 620 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in bed and breakfast rentals in Caledon?

    Experience the best of Caledon with our bed and breakfast rentals, starting at about $20 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Caledon?

    Four-legged friends are welcome in Caledon. Choose from more than 230 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Caledon?

    Yes! Work meets play with ease at over 870 vacation rentals in Caledon featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there Caledon house rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 50 house rentals with pools in Caledon, available on Airbnb. Make a splash and soak up the sun in style!

  • Where should I stay in Caledon?

    Make yourself at home in Caledon by choosing from our most frequently booked neighborhoods. We have over 320 vacation rentals in Snelgrove, and over 320 vacation rentals in Heart Lake.

  • Do bed and breakfast rentals in Caledon have air conditioning?

    Absolutely! We offer over 10 bed and breakfast rentals with air conditioning in Caledon. Enjoy a tailored experience with all the comforts you desire.

  • Do bungalow rentals in Caledon have a kitchen?

    Absolutely! We offer over 20 bungalow rentals with a kitchen in Caledon. Enjoy a tailored experience with all the comforts you desire.

  • Do guesthouse rentals in Caledon have wifi?

    Absolutely! We offer over 30 guesthouse rentals with wifi in Caledon. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Caledon have free parking?

    Absolutely! We offer over 160 apartment rentals with free parking in Caledon. Enjoy a tailored experience with all the comforts you desire.

Quick stats about vacation rentals in Caledon

  • Total vacation rentals

    Explore 1,710 vacation rentals in Caledon

  • Nightly prices starting at

    Caledon vacation rentals start at G$2,092 GYD per night before taxes and fees

  • Verified guest reviews

    Over 35,780 verified reviews to help you choose

  • Family-friendly vacation rentals

    620 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 230 rentals that welcome pets

  • Vacation rentals with a pool

    80 properties feature pools

  • Rentals with dedicated workspaces

    870 properties have a dedicated workspace

  • Wi-Fi availability

    1,620 of Caledon vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Caledon rentals

  • 4.7 Average rating

    Caledon stays receive an average rating of 4.7 out of 5 from guests

  • Nearby attractions

    Caledon's top spots, include SilverCity Brampton Cinemas, Landmark Cinemas 7 Bolton, and Uptown Theatre

Destinations to explore

  1. Airbnb
  2. Canada
  3. Ontario
  4. Peel
  5. Caledon