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Vacation rentals in Caledon

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Caledon

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

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Guest favorite
A spacious basement kitchen is equipped with modern appliances, including a stainless-steel fridge and stove. The central island features two bar stools for casual dining. A comfortable living area is visible, highlighted by a large TV and a stylish electric fireplace. Natural light enters through small windows.
Apartment in Caledon
4.97 out of 5 average rating, 35 reviews

The Luxe Hideout - Guest Suite Basement Apartment

Enjoy The Luxe Hideout - Brand New Basement Guest Suite Apartment for Comfort and Entertainment with Luxury Features and finishes. Perfect Stay for Couples, Solo and Business Travelers. Nearby many amenities, Restaurants, Shopping, activities, and attractions, parks, trails, gym, Community Centre, Walking Distance to Grocery Store. Travel and commute with Ease: 25 Minutes to Pearson Airport, 5 min to major Hwy 410, and nearby Major Cities, public transportation. 50 mins to Downtown Toronto.

Top guest favorite
A tranquil pond is surrounded by lush greenery and features fountains that gently spray water into the air. The area is well-maintained, providing a serene landscape for relaxation and contemplation.
Apartment in Erin
5 out of 5 average rating, 69 reviews

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.

Superhost
Home in Caledon
5 out of 5 average rating, 4 reviews

Luxury 3BR Caledon Retreat | Gym • Spotless Stay

Welcome to our 3BR, 3.5 Bath House in Caledon, featuring: ✓ Driving distance to Toronto Pearson Airport & Toronto Premium Outlet. ✓ 3 spacious bedrooms + 3.5 washroom ✓ Fully equipped kitchen with essentials ✓ Open-concept layout with modern décor ✓ Large flat-screen TV, High-Speed Wi-Fi & Treadmill for workout ✓ Dedicated Workspace ✓ Convenient location, safe neighbourhoods, easy access to major highways ✓ Comfortable bedrooms with high-quality linens for a restful night sleep ✓ Free parking

Top guest favorite
Place to stay in Grand Valley
5 out of 5 average rating, 17 reviews

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.

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, 142 reviews

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.

Top guest favorite
An open-concept living area features a modern kitchen with stainless steel appliances and a dining table for four. A cozy seating arrangement is positioned around a simple coffee table, while a mounted television and wooden accent wall enhance the contemporary design.
Home in Orangeville
4.97 out of 5 average rating, 35 reviews

Orangeville 3BDRM House

This home can accommodate an escape from the city to relax/explore or offer a quiet place to work or recharge if on a business trip. This clean & cozy townhouse is perfect for the whole family. Enjoy a full kitchen stocked with coffee, sugar, honey & spices. The dining area sits 4 with some bonus additional seating at the nearby island. The living room has a large couch with 2 additional seating options that have a clear view of the television. There are 3 fantastic spacious bedrooms.

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
4.91 out of 5 average rating, 150 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.

Guest favorite
A well-lit bedroom features a spacious bed with crisp white linens and neatly arranged towels. Two nightstands with lamps are positioned on either side, while a stylish framed piece of art decorates the wall. A mirrored closet adds a touch of spaciousness to the room.
Guesthouse in Caledon
5 out of 5 average rating, 14 reviews

Cozy Private Basement Bedroom with ensuite

Welcome to your cozy getaway! Perfect for solo travelers, couples & families, this modern space prioritizes comfort & peace of mind for both short & long stays. Enjoy free WiFi & free parking. Prime location makes it a convenient choice: - 15 mins to 3 GO stations - 14 mins drive to DT Brampton - 40 mins drive & 45 mins train to DT Toronto - Easy access to highways (401/407) - 25 mins drive to YYZ Airport - 5 mins to groceries & local restaurants Relax in a safe, welcoming neighborhood!

Guest favorite
Home in Caledon
4.86 out of 5 average rating, 146 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 stone fireplace is set into a rustic wall made of various sized natural stones, providing a textured and earthy backdrop. A flat-screen TV is mounted above, and a wooden cabinet is positioned to the left, adding warmth to the living space.
Apartment in Caledon
4.95 out of 5 average rating, 95 reviews

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.

Top guest favorite
A spacious living area is equipped with a large sectional sofa and a rounded ottoman. A flat-screen television is mounted on the wall, while a mirror reflects natural light from the sliding glass doors leading to an outdoor patio. Plants are arranged to enhance the decor.
Cabin in Orangeville
4.97 out of 5 average rating, 179 reviews

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.

Top guest favorite
The exterior of a tiny home is presented, featuring large glass panels that allow natural light to fill the interior. An open door reveals a glimpse of the modern decor inside. Surrounding greenery adds to the serene atmosphere of the property.
Tiny home in Arthur
4.97 out of 5 average rating, 323 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.

Popular amenities for Caledon vacation rentals

When is the best time to visit Caledon?

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Frequently Asked Questions

  • How much does it cost to stay in villa rentals in Caledon?

    Experience the best of Caledon with our villa rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • What are the most popular amenities for Guesthouse Rentals in Caledon?

    Enhance your stay in our Guesthouse Rentals with the most popular amenities: over 20 homes with a kitchen, over 30 homes with wifi, over 20 homes with air conditioning, over 30 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there family-friendly cottage rentals in Caledon?

    Caledon has more than 10 family-friendly cottage rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Are there pet-friendly apartment rentals in Caledon?

    Four-legged friends are welcome in Caledon. Choose from more than 30 apartment rentals for guests traveling with pets.

  • Are there Caledon house rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 40 house rentals with pools in Caledon, available on Airbnb. Make a splash and soak up the sun in style!

  • Do house rentals in Caledon have air conditioning?

    Absolutely! We offer over 1,000 house rentals with air conditioning in Caledon. Enjoy a tailored experience with all the comforts you desire.

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

    Yes! Work meets play with ease at over 520 house rentals in Caledon featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Where should I stay in Caledon?

    Make yourself at home in Caledon by choosing from our most frequently booked neighborhoods. We have over 10 vacation rentals in Hillsburgh, over 180 vacation rentals in Bolton, and over 700 vacation rentals in Madoc.

  • Do cottage rentals in Caledon have wifi?

    Absolutely! We offer over 10 cottage rentals with wifi in Caledon. Enjoy a tailored experience with all the comforts you desire.

  • Do condo rentals in Caledon have a kitchen?

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

Quick stats about vacation rentals in Caledon

  • Total vacation rentals

    Explore 1,680 vacation rentals in Caledon

  • Nightly prices starting at

    Caledon vacation rentals start at € 9 per night before taxes and fees

  • Verified guest reviews

    Over 35,790 verified reviews to help you choose

  • Family-friendly vacation rentals

    630 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 250 rentals that welcome pets

  • Vacation rentals with a pool

    80 properties feature pools

  • Rentals with dedicated workspaces

    820 properties have a dedicated workspace

  • Wi-Fi availability

    1,600 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 Region
  5. Caledon