Vacation rentals in Caledon

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Top-rated vacation rentals in Caledon

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Guest favorite

Dome in Bradford West Gwillimbury

4.98 out of 5 average rating, 208 reviews

Four season glamping dome under the stars

Whether you are looking for a romantic getaway for two, a solo remote work week in solitude surrounded by nature, or a family adventure, this 4-season geodesic dome is just the right place. Explore picturesque trails of Scanlon Creek Conservation Area, enjoy inground pool in summer, experience breathtaking sunsets over the farm fields, the starry skies by the bonfire, mesmerizing dance of fireflies in June, and let the frogs and crickets lull you to sleep in the place where time stands still...

Nov 12 – 19

€ 126 per night

Guest favorite

Tiny home in Acton

4.98 out of 5 average rating, 194 reviews

Farmview Sunset Cabin

Welcome to our tiny Farmview Cabin that is nestled in the middle of our private oasis located in Acton ON. Our 50 acre farm has spectacular views from every direction. Our horses, , swans, and miniature goats are here to greet you as well. This unique space will allow you to enjoy the beautiful outdoors during the day and a cozy warm space in the evenings! Continental Breakfast fixings are included. We are more than happy to accommodate vegan/plant based/gluten free meals as well.

Oct 31 – Nov 7

€ 139 per night

Guest favorite

Tiny home in Belwood

4.93 out of 5 average rating, 191 reviews

Uniquely Pure Bunkie Getaway in Belwood

Stay on a quiet property amongst trees at the Uniquely Pure Bunkie in Belwood. Enjoy your own space with a firepit, a cozy place to sleep, and a seasonally available outdoor shower (closes Oct 1st until spring). The owner lives on same property as Uniquely Pure Studio, where you can book massage therapies & yoga classes, or purchase products from our aromatherapy and culinary creations line during your stay (contact in advance for availability). Sorry, NO KIDS (for safety) & NO PETS!

Jan 2 – 9

€ 94 per night

Guest favorite

Guest suite in Orangeville

4.92 out of 5 average rating, 656 reviews

Private Hot Tub - Headwaters Retreat

Escape to our cozy and rustic queen suite with a modern touch. Private entrance & hot tub steps from your door, overlooking our peaceful conservation area. Spacious fireplace in main suite with en-suite bathroom, Apple TV, Netflix, and second bedroom with two twin beds. Steps from the hiking trails and just minutes from the town center. Perfect for outdoor adventures, art gallery visits, wine tours, weddings, sporting events, work trips or just a quiet getaway. Your getaway awaits!

Dec 8 – 15

€ 83 per night

Guest favorite

Shipping container in Caledon

4.93 out of 5 average rating, 15 reviews

High Meadows Escape

Enjoy a cozy and quiet winter getaway before the holidays! A beautiful view of the blanket of snow covering the surrounding forest, a crackling fire inside or out and twinkling lights in this serene escape. Hidden among acres of forest, enjoy your private, tranquil, nature escape. Located upon a hill, with a private deck to enjoy meals overlooking the pond. Enjoy this escape no matter the season, indulging in cozy fire nights, skiing, snowshoeing, hiking, picnics and so much more.

Dec 17 – 24

€ 122 per night

Guest favorite

Cabin in Erin

4.94 out of 5 average rating, 275 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!

Mar 20 – 27

€ 251 per night

Guest favorite

Guest suite in Mono

4.98 out of 5 average rating, 65 reviews

Welcome to a Sweet Suite

Forget your worries in this spacious and serene space. Enjoy the hiking trails at Mono Cliffs and Island Lake or an afternoon of wine tasting at Adoma Winery. Golf/ski is only 5km away at beautiful Hockley Valley. Enjoy a 5 star dinner at one of the fabulous restaurants in Orangeville. After a busy day return to your cozy queen size bed for a great night sleep. In the morning no need to head out for coffee as it is available for brewing on site. Cream and sugar provided.

Jun 13 – 20

€ 89 per night

Guest favorite

Cabin in Mono

4.94 out of 5 average rating, 272 reviews

The Trails Retreat (Private Cabin)

Beautifully renovated 2-story private hilltop cabin for romantic getaway, family stay or friends' retreat, experience a taste of the country together. Backed by forest and trails and set away from our family home and yoga studio, minutes to the Bruce Trail, Hockley Ski & Resort, and Mansfield Ski Club, enjoy total guest privacy & spectacular sunrises. Guests are welcome to share our heated pool in season:) Chef's creations and Private yoga and group classes available

Dec 2 – 9

€ 178 per night

Guest favorite

Guest suite in Mono

4.98 out of 5 average rating, 268 reviews

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.

Aug 28 – Sep 4

€ 110 per night

Guest favorite

Apartment in Caledon

4.93 out of 5 average rating, 69 reviews

Separate apartment with pool, on golf course.

This is a comfortable, newly renovated studio apartment with separate entrance and private inground pool. It is decorated with Restoration Hardware furniture, features a fully-functioning kitchen, and access to a patio with outdoor barbeque. It is nestled in a tranquil setting on the back of the Caledon Woods golf course with easy access to highways leading to Toronto, Pearson International Airport (30 minutes), and the Caledon Equestrian Park (5 minutes).

Oct 17 – 24

€ 86 per night

Guest favorite

Guest suite in Caledon

4.98 out of 5 average rating, 89 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

Oct 4 – 11

€ 108 per night

Guest favorite

Guesthouse in Schomberg

4.93 out of 5 average rating, 342 reviews

Country Cabin for Long and Short Stays Queen bed

Our Country Cabin get-away is perfect for those looking to get out of the city and back to nature for a short or extended stay! Enjoy a little winter getaway and share our paradise in the countryside and be part of it all. You’ll love our location, full kitchen, access to camp fire pit, propane bbq, wifi internet, 40" Smart TV, three piece bathroom, laundry facilities and more.

May 17 – 24

€ 117 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Caledon vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Caledon's top sights

Bramalea City Centre64 locals recommend

Trinity Common Mall26 locals recommend

Albion Hills Conservation Park15 locals recommend

Chinguacousy Park41 locals recommend

Cassie Campbell Community Centre7 locals recommend

William Osler Health System - Brampton Civic Hospital4 locals recommend

Other great vacation rentals in Caledon

Guest favorite

Guesthouse in Mono

4.92 out of 5 average rating, 89 reviews

Mono Studio

Sep 20 – 27

€ 110 per night

Guest favorite

Guesthouse in Orangeville

4.97 out of 5 average rating, 98 reviews

A bright & stylish urban studio

Sep 8 – 15

€ 76 per night

Guest favorite

Loft in Mono

4.98 out of 5 average rating, 59 reviews

Hockley Haven

Jul 11 – 18

€ 105 per night

Guest favorite

Farm stay in Loretto

4.92 out of 5 average rating, 26 reviews

Character-filled farm guest house on 8 acres

Sep 27 – Oct 4

€ 128 per night

Guest favorite

Bungalow in Terra Cotta

4.99 out of 5 average rating, 86 reviews

Country Cottage House, Cozy and Private

Aug 18 – 25

€ 144 per night

Guest favorite

Guesthouse in Halton Hills

4.87 out of 5 average rating, 31 reviews

The Clayhill Bunkie

Feb 16 – 23

€ 67 per night

Guest favorite

Apartment in Caledon

5.0 out of 5 average rating, 11 reviews

Caledon Getaway

Jan 27 – Feb 3

€ 127 per night

Guest favorite

Home in Orangeville

4.78 out of 5 average rating, 49 reviews

A Modern 3 Bedroom Home with Free Parking & Wifi

Nov 8 – 15

€ 124 per night

Show all

Quick stats about vacation rentals in Caledon

Total rentals
1.7K properties
Rentals with dedicated workspaces
910 properties have a dedicated workspace
Rentals with a pool
80 properties have a pool
Pet-friendly rentals
260 properties allow pets
Family-friendly rentals
570 properties are a good fit for families
Total number of reviews
28K reviews

Frequently Asked Questions

How much does it cost to stay in townhouse rentals in Caledon?
Experience the best of Caledon with our townhouse 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.
What are the most popular amenities for Private Suite Rentals in Caledon?
Enhance your stay in our Private Suite Rentals with the most popular amenities: over 10 homes with a gym, over 130 homes with wireless internet, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there family-friendly vacation rentals in Caledon?
Caledon has more than 570 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Are there pet-friendly vacation rentals in Caledon?
Four-legged friends are welcome in Caledon. Choose from more than 260 vacation rentals for guests traveling with pets.
Do townhouse rentals in Caledon have wireless internet?
Absolutely! We offer over 70 townhouse rentals with wireless internet in Caledon. Enjoy a tailored experience with all the comforts you desire.
Are there Caledon vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 80 vacation homes with pools in Caledon, available on Airbnb. Make a splash and soak up the sun in style!
Are there vacation rentals with a dedicated workspace in Caledon?
Yes! Work meets play with ease at over 910 vacation 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 160 vacation rentals in Bolton, over 10 vacation rentals in Mono Mills, over 350 vacation rentals in Snelgrove, and over 750 vacation rentals in Madoc.
Do apartment rentals in Caledon have self check-in?
Absolutely! We offer over 20 apartment rentals with self check-in in Caledon. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Caledon have a gym?
Absolutely! We offer over 80 house rentals with a gym in Caledon. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in Caledon

Top-rated vacation rentals in Caledon

Vacation rentals for every style

Houses

Apartments

Hotels

Popular amenities for Caledon vacation rentals

Stay near Caledon's top sights

Other great vacation rentals in Caledon

Guesthouse in Mono

Guesthouse in Orangeville

Loft in Mono

Farm stay in Loretto

Bungalow in Terra Cotta

Guesthouse in Halton Hills

Apartment in Caledon

Home in Orangeville

Quick stats about vacation rentals in Caledon

Total rentals

Rentals with dedicated workspaces

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

How much does it cost to stay in townhouse rentals in Caledon?

What are the most popular amenities for Private Suite Rentals in Caledon?

Are there family-friendly vacation rentals in Caledon?

Are there pet-friendly vacation rentals in Caledon?

Do townhouse rentals in Caledon have wireless internet?

Are there Caledon vacation rentals on Airbnb with pools?

Are there vacation rentals with a dedicated workspace in Caledon?

Where should I stay in Caledon?

Do apartment rentals in Caledon have self check-in?

Do house rentals in Caledon have a gym?

Destinations to explore