Vacation rentals with outdoor seating in Caledon

Find and book unique outdoor seating rentals on Airbnb

Top-rated outdoor seating rentals in Caledon

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Guest favorite

Guesthouse in Orangeville, Canada

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 18 – 25

G$30,927 GYD per night

Guest favorite

Tiny home in Mulmur, Canada

4.98 out of 5 average rating, 120 reviews

Paradise Pines Bunkie in Woodland Acres

Experience this nature retreat just 60 km from Toronto and feel like you’re thousands of miles away. The perfect glamping experience for any nature lover looking for a relaxing getaway. There is power in the bunkie which offers the convenience of lighting, cell phone charging, an electric fireplace, a kuerig coffee maker and mini fridge with freezer. Pursue your favourite outdoor activities during the day and then return to your cozy queen size bed and sofa bed just steps away from the bonfire.

Sep 24 – Oct 1

G$24,136 GYD per night

Guest favorite

Place to stay in Wasaga Beach

5.0 out of 5 average rating, 191 reviews

Newly Built Woodsy Loft Retreat

Welcome to Woodsy Loft, a newly built retreat. A great spot for a getaway! A perfect home base for not just the beach and stunning walks into the sunset, but Blue Mtn, Scandinavian Spa, Collingwood, Cross Country Skiing Provincial Park and a brand new casino, all close by. Packed with amenities like screened in patio, XL bathtub, King size bed, 'The Frame' Smart TV, full kitchen, fast WIFI, motorized blind...and the list goes on. Situated and designed to offer max. privacy and relaxation.

Jan 2 – 9

G$29,419 GYD per night

Guest favorite

Guesthouse in Acton

4.97 out of 5 average rating, 229 reviews

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.

Jul 19 – 26

G$57,401 GYD per night

Guest favorite

Tiny home in Acton

4.98 out of 5 average rating, 196 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.

Mar 26 – Apr 2

G$30,552 GYD 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.

May 29 – Jun 5

G$20,569 GYD per night

Guest favorite

Tiny home in Belwood

4.93 out of 5 average rating, 192 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!

Jul 19 – 26

G$18,179 GYD per night

Guest favorite

Farm stay in Essa, Canada

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!

Dec 11 – 18

G$35,733 GYD per night

Guest favorite

Apartment in Fergus

4.95 out of 5 average rating, 132 reviews

Riverside Retreat

One bedroom self-contained apartment right on the bank of the Grand River in historic Fergus, Ontario. Very quiet. Spacious screened porch next to Grand River! Fifteen minutes walk (or less than five minutes drive) to downtown Fergus. Beautiful downtown Elora, Elora Gorge Conservation Area and Belwood Lake Conservation Area are all within a ten minute drive. Note that access is down a flight of exterior stairs and unfortunately is not suited for individuals with mobility challenges.

Jul 2 – 9

G$17,348 GYD 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

G$15,643 GYD per night

Guest favorite

Cabin in Erin

4.94 out of 5 average rating, 277 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 27 – Feb 3

G$49,093 GYD per night

Guest favorite

Farm stay in Lincoln

4.97 out of 5 average rating, 349 reviews

Water Edge, Modern Log Cabin in Beautiful Orchards

Nestled among Niagara’s fruit trees, our newly renovated log cabin sits on the shores of 16 Mile Creek. The log cabin is a modern, meticulously maintained studio space, secluded from busy roads (perfect to work in). Relax with a morning coffee on our porch or enjoy an evening campfire while overlooking 16 Mile Creek. Amenities include a comfortable sitting area, large picture windows, kitchenette (with hotplate), breakfast bar, elegant bathroom, BBQ and more.

Dec 26 – Jan 2

G$28,701 GYD per night