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.

Guest favourite
Dome in Bradford West Gwillimbury
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...
Sep. 29 – Oct. 6
$184 CAD per night
4.98 out of 5 average rating, 198 reviews
Guest favourite
Apartment in Orangeville
A bright & modern urban studio
Come & unwind...in comfort. "The Snug" is a 740 square foot studio-style unit, that is bright & modern. You will be on the basement level of the main house, with a completely separate entrance. Amazing kitchen, sleek 3 pc bathroom with rainfall shower head. The queen bed with luxury-firm mattress, has built in storage for all your needs. Dinner table expands for meals, games or working at home! A short hop from Toronto, Dufferin County has all you need for a relaxing getaway! Come & See :)
Jan. 2 – 9
$113 CAD per night
4.98 out of 5 average rating, 49 reviews
Guest favourite
Guesthouse in Acton
Wooden guesthouse in the forest
The guesthouse is the perfect getaway. Like living at a cottage, minutes away from the city. This loft guest house is fully equipped with a bedroom, own kitchen, and private bathroom. We are just 45 minutes from Toronto with a short drive to both Georgetown & Acton. Ten Minutes To 401. This retreat is nestled on a hill with spectacular views, surrounded by 16 acres of towering trees overlooking a creek with a private waterfall and walking trails. Perfect for photographers and influencers.
Apr. 16 – 23
$326 CAD per night
4.97 out of 5 average rating, 223 reviews

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 favourite
Cottage in Mono
Hockley Riverside Cottage • Loft and Bunkie
Apr. 21 – 28
$269 CAD per night
4.92 out of 5 average rating, 50 reviews
Guest favourite
Guesthouse in Halton Hills
The Clayhill Bunkie
Jun. 1 – 8
$108 CAD per night
4.85 out of 5 average rating, 27 reviews
Guest favourite
Guesthouse in Mono
Mono Studio
Sep. 6 – 13
$163 CAD per night
4.94 out of 5 average rating, 83 reviews
Guest favourite
Apartment in Orangeville
Beautiful Getaway in Orangeville
Apr. 22 – 29
$157 CAD per night
5.0 out of 5 average rating, 36 reviews
Guest favourite
Guest suite in Orangeville
Garden Studio Apartment
Jul. 5 – 12
$143 CAD per night
5.0 out of 5 average rating, 66 reviews
Guest favourite
Home in Alton
The Potters Cottage
Aug. 4 – 11
$310 CAD per night
5.0 out of 5 average rating, 35 reviews
Guest favourite
Loft in Erin
Tree Top Oasis
May 8 – 13
$210 CAD per night
4.98 out of 5 average rating, 97 reviews
Guest favourite
Cabin in Orangeville
Hockley Valley Cozy Cottage
Jan. 21 – 28
$278 CAD per night
4.98 out of 5 average rating, 63 reviews
Guest favourite
Guest suite in Caledon
Beautiful Retreat in Caledon
Dec. 13 – 20
$324 CAD per night
5.0 out of 5 average rating, 13 reviews
Guest favourite
Apartment in Caledon
Separate apartment with pool, on golf course.
Jul. 19 – 26
$126 CAD per night
4.93 out of 5 average rating, 68 reviews
Guest favourite
Home in Kleinburg
Charming Log Home - 25 private acres in Caledon
Nov. 3 – 10
$564 CAD per night
5.0 out of 5 average rating, 32 reviews
Guest favourite
Apartment in Bolton
Newly built Bolton Studio
Sep. 4 – 11
$112 CAD per night
4.92 out of 5 average rating, 24 reviews

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

Destinations to explore