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, 213 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...

Mar 2 – 9

ﺩ.ﺇ439 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.

Aug 14 – 21

ﺩ.ﺇ526 per night

Guest favorite

Tiny home in Acton

4.98 out of 5 average rating, 195 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.

Apr 17 – 24

ﺩ.ﺇ536 per night

Guest favorite

Farm stay in Essa

5.0 out of 5 average rating, 118 reviews

The Schoolhouse

Kick back and relax in this calm, stylish space. This school portable turned into a modern guest home is situated on acreage boasting with gorgeous views of forests, fields, grazing animals and sunsets. In warmer months, cool off in the stock tank pool, play on the volleyball court, and enjoy meals on the deck accessed from the bedroom and main entry. Relax by the campfire, walk nearby trails, visit restaurants, markets and shops. Planning your wedding? Ask about our wedding package!

Nov 4 – 11

ﺩ.ﺇ627 per night

Guest favorite

Guesthouse in Orangeville

4.97 out of 5 average rating, 98 reviews

A bright & stylish urban studio

Come & relax...in privacy. The "Carriage House" is a 634 square foot studio-style unit is unique & intimate. You will be away from the main house, in your own building. Amazing kitchen, complete with gas range. Spacious & elegant over-sized bathroom. The Murphy bed has a luxury-firm queen mattress, & stows away in a snap for your convenience. Diner booth for meals, or working at home! A short hop from Toronto, Dufferin County has all you need for a relaxing getaway! Come & See :)

Mar 11 – 18

ﺩ.ﺇ254 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

ﺩ.ﺇ275 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.

May 20 – 27

ﺩ.ﺇ429 per night

Guest favorite

Cabin in Erin

4.94 out of 5 average rating, 276 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!

Jan 25 – Feb 1

ﺩ.ﺇ862 per night

Guest favorite

Guesthouse in Mono

4.92 out of 5 average rating, 90 reviews

Mono Studio

Located in the beautiful Island Lake Estates community. The Mono studio is a private cozy little getaway from the hustle and bustle. The studio is surrounded by amenities that offer something for everyone. Enjoy wine tasting at Adamo Estates, take a walk on the Vicky Barron Trail, visit Mono Cliffs Park, ski or golf at Hockley Valley Resort or venture into Orangeville for some great local restaurants or a show at the Orangeville Theater. Twin bed expands to King size

Sep 16 – 23

ﺩ.ﺇ381 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 25 – Jan 1

ﺩ.ﺇ613 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.

Jun 17 – 24

ﺩ.ﺇ331 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).

Sep 3 – 10

ﺩ.ﺇ307 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

Guest suite in Mono

4.98 out of 5 average rating, 66 reviews

Welcome to a Sweet Suite

Sep 7 – 14

ﺩ.ﺇ294 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

Aug 10 – 17

ﺩ.ﺇ449 per night

Guest favorite

Cabin in CALEDON EAST

4.91 out of 5 average rating, 74 reviews

Bunkie in the Forest

Sep 6 – 13

ﺩ.ﺇ476 per night

Guest favorite

Bungalow in Terra Cotta

4.99 out of 5 average rating, 86 reviews

Country Cottage House, Cozy and Private

Aug 22 – 29

ﺩ.ﺇ470 per night

Guest favorite

Guest suite in Orangeville

5.0 out of 5 average rating, 75 reviews

Garden Studio Apartment

Jan 10 – 17

ﺩ.ﺇ344 per night

Guest favorite

Loft in Mono

4.97 out of 5 average rating, 60 reviews

Hockley Haven

Oct 12 – 19

ﺩ.ﺇ411 per night

Guest favorite

Guesthouse in Halton Hills

4.88 out of 5 average rating, 32 reviews

The Clayhill Bunkie

Apr 12 – 19

ﺩ.ﺇ223 per night

Guest favorite

Apartment in Caledon

5.0 out of 5 average rating, 11 reviews

Caledon Getaway

May 14 – 21

ﺩ.ﺇ496 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 bed and breakfast rentals in Caledon?
Experience the best of Caledon with our bed and breakfast rentals, starting at about $10 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 Cabin Rentals in Caledon?
Enhance your stay in our Cabin Rentals with the most popular amenities: over 10 homes with wireless internet, over 10 homes with a bbq area, 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 350 vacation rentals in Snelgrove, over 750 vacation rentals in Madoc, over 160 vacation rentals in Bolton, and over 10 vacation rentals in Mono Mills.
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 private suite rentals in Caledon have a gym?
Absolutely! We offer over 10 private suite 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

Guest suite in Mono

Farm stay in Loretto

Cabin in CALEDON EAST

Bungalow in Terra Cotta

Guest suite in Orangeville

Loft in Mono

Guesthouse in Halton Hills

Apartment in Caledon

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 bed and breakfast rentals in Caledon?

What are the most popular amenities for Cabin 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 apartment rentals in Caledon have self check-in?

Do private suite rentals in Caledon have a gym?

Destinations to explore