Vacation rentals with outdoor seating in Caledon

HotTub & Pool Getaway - Headwaters Retreat

Escape to our rustic-modern Queen Suite, perfect for your getaway. Relax in the private hot tub right outside your door, unwind by the fireplace & enjoy Netflix & Amazon TV. This cozy retreat features a private entrance, ensuite bathroom, and a second bedroom with twin beds. Steps from scenic hiking trails, minutes from the town center, your stay is ideal for outdoor adventures, wine tours, weddings, work trips or just quiet escape away. Book now for your ultimate getaway in comfort and nature!

Hockley Haven

Kick back and relax in this calm, stylish space. Newly renovated cozy 1 bedroom carriage house loft (appx 650 sq ft) above detached 3 bay garage in serene country setting on 5 acres of pine and cedar with a river running thru it. Pullout couch can accommodate 2 additional people. Walk across the road to Pollinator Garden & Island Lake Trails. 6 min drive to Hockley Valley Resort and Adamo Estate Winery, as well as beautiful downtown Orangeville boasting fabulous restaurants and quaint shops.

Hockley Valley Cozy Cottage

Take it easy at this unique and tranquil setting where the entire property is yours! Freshly renovated cottage only 600M from Hockley Valley Resort and also close to restaurants and hiking trails. This cottage sleeps 4 comfortably with separate bedroom. Picturesque setting directly on Nottawasaga river with mature gardens and plenty of outdoor space. Morning coffee or afternoon drinks under the covered gazebo at the waters edge or relax in the hammocks, this place truly has it all.

The Clayhill Bunkie

Looking for a place to get away that’s semi off-grid or a place that’s kind of like glamping? The Clayhill Bunkie is just the place and minutes from Silvercreek & Terra Cotta Conservation areas, the Credit River, the villages of Glen Williams and Terra Cotta, and the town of Georgetown. Spend your day hiking, cycling, antique hunting, tubing, or site seeing, then order in or grab some take-out and come relax by a roaring fire. Firewood is included, adding great value to your stay.

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!

Mono — Cabin in the Woods Experience

This cozy cabin in the woods is perfect for content creation, photography, proposals or just enjoying nature and swimming in the summer or ice skating throughout the winter. Only minutes from Orangeville, Hockley Valley and less than one hour from downtown Toronto you feel hours away from everything. Swim in your private pond, recharge and escape the noise of the city and relax in your own personal paradise! Cabinonthe9 is one of Canada's top short term rental destinations.

Rural Estate Coach House Apartment

Peaceful secluded guest house in forest property 5 minutes from Orangeville. 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.

Hockley valley, up country guest cottage

please read the entire post our beautiful cottage is located on 27 acres of land. Which is very secluded and quiet. Open concept cottage , with a loft bedroom with a double bed, a double sofa bed and a single folding bed. Wood burning fire place and a Small area with a hot plate , microwave, toaster oven, coffee maker , small fridge , BBQ on the porch. Swimming pond Vegetable garden and honey bees. Beautiful wooded trail No smoking Kids are welcome

Waterfront Coach House Loft

This friendly, private open concept loft apartment is located on the top floor of a guest coach house located on a 2 acre waterfront estate. The loft apartment is a separate building from the main house. There is a maximum occupancy for the loft of 2 people, parties, get togethers and events are not permitted. Due to the tall spiral staircase, children are not permitted due to safety. Extra charges will apply if additional guests are present in the loft.