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.

Guest favorite

Dome in Bradford West Gwillimbury

4.98 out of 5 average rating, 201 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 17 – 24

$106 per night
Guest favorite

Guesthouse in Orangeville

4.96 out of 5 average rating, 309 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.

Jun 24 – Jul 1

$121 per night
Guest favorite

Tiny home in Acton

4.98 out of 5 average rating, 192 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.

Jul 15 – 22

$133 per night

Popular amenities for Caledon vacation rentals

Stay near Caledon's top sights

Bramalea City Centre64 locals recommend
Trinity Common Mall26 locals recommend
Chinguacousy Park41 locals recommend
Albion Hills Conservation Park15 locals recommend
William Osler Health System - Brampton Civic Hospital4 locals recommend
Island Lake Conservation Area31 locals recommend

Other great vacation rentals in Caledon

Guest favorite

Apartment in Caledon

4.93 out of 5 average rating, 69 reviews

Separate apartment with pool, on golf course.

Sep 10 – 17

$73 per night
Guest favorite

Loft in Mono

4.98 out of 5 average rating, 58 reviews

Hockley Haven

Jul 23 – 30

$95 per night
Guest favorite

Bungalow in Terra Cotta

4.99 out of 5 average rating, 86 reviews

Country Cottage House, Cozy and Private

Sep 6 – 13

$112 per night
Guest favorite

Guesthouse in Halton Hills

4.85 out of 5 average rating, 27 reviews

The Clayhill Bunkie

Feb 28 – Mar 7

$53 per night
Guest favorite

Guest suite in Orangeville

5.0 out of 5 average rating, 69 reviews

Garden Studio Apartment

Nov 15 – 22

$83 per night
Guest favorite

Loft in Erin

4.98 out of 5 average rating, 98 reviews

Tree Top Oasis

Apr 16 – 21

$122 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

Nov 8 – 15

$113 per night
Superhost

Bungalow in Caledon

4.86 out of 5 average rating, 7 reviews

Escarpment Apartments

Jun 16 – 23

$75 per night
Guest favorite

Guesthouse in Erin

4.78 out of 5 average rating, 23 reviews

Guest Suite (Basement) in Erin- Hiker's paradise.

Feb 25 – Mar 4

$59 per night
Guest favorite

Apartment in Orangeville

5.0 out of 5 average rating, 36 reviews

Beautiful Getaway in Orangeville

Sep 28 – Oct 5

$93 per night
Guest favorite

Guest suite in Caledon

5.0 out of 5 average rating, 13 reviews

Beautiful Retreat in Caledon

Aug 4 – 11

$161 per night
Guest favorite

Apartment in Caledon

5.0 out of 5 average rating, 10 reviews

Caledon Getaway

Nov 11 – 18

$110 per night

Quick stats about vacation rentals in Caledon

Total rentals

1.6K properties

Rentals with dedicated workspaces

870 properties have a dedicated workspace

Rentals with a pool

80 properties have a pool

Pet-friendly rentals

270 properties allow pets

Family-friendly rentals

590 properties are a good fit for families

Total number of reviews

28K reviews

Frequently Asked Questions

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

    Experience the best of Caledon with our condo rentals, starting at about $50 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 self check-in, over 80 homes with a bbq area, over 70 homes with a gym, over 930 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 590 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 270 vacation rentals for guests traveling with pets.

  • Do bed and breakfast rentals in Caledon have wireless internet?

    Absolutely! We offer over 20 bed and breakfast 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 870 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 320 vacation rentals in Snelgrove, over 10 vacation rentals in Mono Mills, over 150 vacation rentals in Bolton, and over 730 vacation rentals in Madoc.

  • Do house rentals in Caledon have self check-in?

    Absolutely! We offer over 80 house rentals with self check-in in Caledon. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Caledon have a gym?

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

Destinations to explore