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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Guest favorite

Dome in Bradford West Gwillimbury

4.98 out of 5 average rating, 216 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...

Apr 17 – 24

ﺩ.ﺇ438 per night

Guest favorite

Guesthouse in Orangeville

4.95 out of 5 average rating, 310 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.

Oct 11 – 18

ﺩ.ﺇ568 per night

Guest favorite

Tiny home in Acton

4.98 out of 5 average rating, 198 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.

Jan 24 – 31

ﺩ.ﺇ535 per night

Guest favorite

Apartment in Mono

4.95 out of 5 average rating, 197 reviews

Rural Estate Coach House Apartment

Peaceful secluded guest house in forest property 5 minutes from Orangeville, 1 hour from downtown Toronto. We have three active dogs who often demand attention! Can be arranged as a two bedroom with privacy or a one bedroom with extra room. King bed in the large bedroom. Double futon in the sitting room. Fabulous bathroom with views. The guest house is 70 feet from main house. Quiet, nice forest walks. NOT a 'corporate Airbnb' - managed by owner. Near Bruce Trail and Hockley.

Nov 9 – 16

ﺩ.ﺇ360 per night

Guest favorite

Tiny home in Belwood

4.93 out of 5 average rating, 193 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!

Dec 27 – Jan 3

ﺩ.ﺇ340 per night

Guest favorite

Guest suite in Orangeville

4.92 out of 5 average rating, 656 reviews

Private HotTub - 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

ﺩ.ﺇ274 per night

Guest favorite

Cabin in Erin

4.94 out of 5 average rating, 283 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!

Feb 9 – 16

ﺩ.ﺇ860 per night

Guest favorite

Cabin in Mono

4.94 out of 5 average rating, 273 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

Nov 20 – 27

ﺩ.ﺇ611 per night

Guest favorite

Guest suite in Mono

4.98 out of 5 average rating, 269 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.

Jul 31 – Aug 7

ﺩ.ﺇ330 per night

Guest favorite

Apartment in Shelburne

5.0 out of 5 average rating, 120 reviews

A&M Cozy Home Away From Home

Bring the whole family to this great place with lots of room for fun. Guests can enjoy this beautiful modern 2 bdrms with queen size beds, legal/separate entrance apartment equipped with kitchen appliances, microwave, stove, dishwasher, fridge, toaster, coffee maker, pots, plates, utensils, separate laundry. Equipped with your comfort in mind. It offers shampoo, conditioner, body wash, towels, keyless entry. Ignite TV premier PKG, Netflix, free 500 mbps Wifi.

Feb 22 – Mar 1

ﺩ.ﺇ295 per night

Guest favorite

Guest suite in Schomberg

4.91 out of 5 average rating, 413 reviews

Romantic Country Suite for Couples with King Bed

Our Country Suite is all about Rustic Elegance. Come to our farm for a night, a weekend, or longer. Perfect place for a quiet, peaceful & relaxing weekend escape or a romantic getaway. You’ll love our rural location, full kitchen, wifi internet, 55" 4K Smart TV, three piece bathroom, laundry, propane BBQ, Patio access to propane fire pit. Enjoy walking trails in our bush, biking, close to nature and much more. Located about 50 min. from Toronto.

Jun 2 – 7

ﺩ.ﺇ416 per night

Guest favorite

Guest suite in Orangeville

4.97 out of 5 average rating, 104 reviews

The Spoke - Private basement apart. near downtown

Cozy basement apartment in family home: nope, not a vintage farmhouse nestled in the countryside but conveniently located in town and close to recreation, shopping, dining, business and special event/banquet locations. Living room, galley kitchen, bedroom with adjacent bathroom. Did we mention it's a basement? Yes, there are some stairs, and an HVAC bulkhead in living room and bedroom w/ 6'2" clearance. Check us out on Instagram at @thespokeov

Jan 6 – 13

ﺩ.ﺇ313 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

Island Lake Conservation Area31 locals recommend

Other great vacation rentals in Caledon

Guest favorite

Farm stay in Essa

4.99 out of 5 average rating, 119 reviews

The Schoolhouse

Mar 4 – 11

ﺩ.ﺇ651 per night

Guest favorite

Loft in Erin

4.98 out of 5 average rating, 101 reviews

Tree Top Oasis

Oct 24 – 29

ﺩ.ﺇ535 per night

Guest favorite

Tiny home in Mulmur

4.98 out of 5 average rating, 120 reviews

Paradise Pines Bunkie in Woodland Acres

Jun 14 – 21

ﺩ.ﺇ433 per night

Guest favorite

Guest suite in Kimberley

4.93 out of 5 average rating, 543 reviews

The Post Office Motel & Spa in the ❤️ of Kimberley

Apr 28 – May 5

ﺩ.ﺇ472 per night

Guest favorite

Guest suite in Caledon

4.98 out of 5 average rating, 92 reviews

Casa Caledon-Secluded Suite Surrounded by Nature

Oct 24 – 31

ﺩ.ﺇ377 per night

Guest favorite

Apartment in Caledon

4.93 out of 5 average rating, 70 reviews

Separate apartment with pool, on golf course.

Sep 9 – 16

ﺩ.ﺇ306 per night

Guest favorite

Shipping container in Caledon

4.88 out of 5 average rating, 17 reviews

High Meadows Escape

Nov 4 – 11

ﺩ.ﺇ428 per night

Guest favorite

Cabin in CALEDON EAST

4.88 out of 5 average rating, 78 reviews

Bunkie in the Forest

Jan 5 – 12

ﺩ.ﺇ488 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 guesthouse rentals in Caledon?
Experience the best of Caledon with our guesthouse 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 House Rentals in Caledon?
Enhance your stay in our House Rentals with the most popular amenities: over 80 homes with a gym, over 80 homes with self check-in, over 80 homes with a bbq area, over 1,040 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 cottage rentals in Caledon have wireless internet?
Absolutely! We offer over 10 cottage 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 750 vacation rentals in Madoc, over 10 vacation rentals in Mono Mills, and over 350 vacation rentals in Snelgrove.
Do bungalow rentals in Caledon have self check-in?
Absolutely! We offer over 10 bungalow 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

Farm stay in Essa

Loft in Erin

Tiny home in Mulmur

Guest suite in Kimberley

Guest suite in Caledon

Apartment in Caledon

Shipping container in Caledon

Cabin in CALEDON EAST

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 guesthouse rentals in Caledon?

What are the most popular amenities for House Rentals in Caledon?

Are there family-friendly vacation rentals in Caledon?

Are there pet-friendly vacation rentals in Caledon?

Do cottage 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 bungalow rentals in Caledon have self check-in?

Do house rentals in Caledon have a gym?

Destinations to explore