Guesthouse vacation rentals in Caledon

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.

A bright & stylish urban studio

Come & relax...in privacy. In the "Carriage House" you will be away from the main house, in your own building! Its a 634 square foot studio-style unit, that is unique & intimate. A nice sized kitchen, complete with gas range. Spacious & bright over-sized bathroom. The Murphy bed has a luxury-firm queen mattress, & stows away in a snap for more room. A 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 :)

Treehouse in the forest

Treehouse in the Forest is the perfect getaway. Like living at a cottage, minutes away from the city. This place is fully equipped with 2 bedrooms, own kitchenete, and private bathroom. We are just 45 minutes from Toronto with a short drive to both Georgetown & Acton. 10 Minutes to 401. This guesthouse 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.

Guesthouse on Lake Ontario Niagara

Please mark this listing as a favourite to get notifications of last minute deals. Unwind at our cozy guest house. Enjoy the direct waterfront views from the living room, bedroom and private Muskoka chairs. We are located along the shore of Lake Ontario amongst the fruit belt of the Niagara region. vineyards, peach, nectarine and plum trees. Shops, Restaurants, and Award Winning Wineries. FREE TESLA charger 🔌 Direct Lakefront OPEN TIMESLOTS TUESDAY JULY 28 (1 night/2 days) discounted one night

Melville Guesthouse

Welcome to The Melville Guesthouse, a charming one-bedroom retreat on a quiet street in Elora. Enjoy the privacy of your yard while being a short walk from downtown, the Elora Centre for the Arts, the river, and historic homes. Whether you’re here for trails, boutique shops, or Elora’s arts and dining scene, our standalone guesthouse offers comfort and convenience—perfect for couples and families, with a pull-out couch for extra guests. Ideally located, you’re near everything Elora offers.

Sweet Studio ~ Spacious Yard ~ Nature Haven ~ AC

Experience a private, urban studio cottage located in a gorgeous tree-filled backyard in the Junction neighbourhood, close to downtown Guelph, with full amenities. Comfortable queen bed, natural gas fireplace, fully stocked kitchen, separate shower, 2-piece washroom, additional sleeping loft, private back flagstone patio, and one complimentary sauna. Located in the heart of the Junction Village intentional community, guests can connect with others, or have a private retreat experience.

“CasaDeLeon”- Modern and cozy Lakeview guesthouse

Forget your worries in this quiet,, spacious & serene space. King+queen air/4 twin , lrg patio doors overlooking lush greenery in private backyard oasis. Enjoy in/outdoor living & access to private basketball court, trampoline. Landscaped backyard w deck, bbq, tons of board games, 4K projector (stream from G00gle chromecast) for large screen media / movies, and wine fridge, espresso bar, fridge w ice maker, full bathroom, heated flooring. IMPORTANT: You MUST read “Other Details To Note”

Carriage House - Elora

Discover a piece of history in Elora, Ontario. This beautiful stone, board & batten private 1-bedroom building was the former carriage house, and is nestled at the rear of the Postmaster's yard. Enjoy the spacious king bed, fireplace, and beautiful garden oasis. Only a 10-minute walk to the downtown. The yard and parking is shared with the Postmaster's House - nothing else is shared! *Please note: the interior space-saving staircase is steep and may not be suitable for all guests*

Bright and Airy Guest Suite with Pool

Large windows, high ceilings, fresh modern decor, cedar sauna, fitness room and backyard pool best describes our Garden Suite. Spoil yourself in everything this space has to offer. Featuring a comfy queen size bed sheeted with luxury cotton and down duvet. A large queen pull-out couch offers space for extra sleepers. Take some time to refine your culinary skills with the well appointed kitchen. Don't overpack, your in-unit washer and dryer will keep your clothes clean.

The Clayhill Bunkie

Semi off-grid bunkie on The Bruce Trail and minutes from Silvercreek & Terra Cotta Cons. areas, the Credit River, Glen Williams, Terra Cotta, & Georgetown. Spend your day hiking, cycling, antique hunting, tubing, or site seeing, then order in or grab take-out and come relax by a fire. 1 basket of wood is included, adding great value. You WILL hear wildlife and farm animals here. Rural property, limited electricity, beautiful views. This is NOT a hotel room.

The Captain's Cottage at Willow Pond

You will have your own private one bedroom cottage on our 17 acre property. Your countryside getaway can be as quiet or as busy as you make it. You will have access to our tennis court, swimming pool, hot tub, gazebo, pond, garden and woodland trails. Adults are welcome to use the exercise studio. There is a flock of heritage chickens, guinea hens and quail who lay beautiful eggs for your breakfast. We also have bees who produce delicious honey for our guests.

Private, sunny cottage steps from downtown Guelph

Our private cottage is steps from downtown Guelph. The cottage is complete with a kitchenette and a bathroom with a large shower. The cottage is a separate building located in our back garden.You access the cottage along the driveway and stone pathway through the back garden. There is free wireless Internet along with Rogers Ignite TV and Netflix. The living room is spacious and there is one bedroom with a king- sized bed.