Guesthouse holiday rentals in Caledon

Cabin in nature Close to trails and Thermea Spa

Relax and unwind at this peaceful and private Guesthouse situated on 25 acres of forest. We are family friendly and invite you to roam the land and visit our ducks and chickens! If you are feeling adventurous, enjoy a hike or bike ride on one of the many local trails within walking distance in the Trail Capital of Canada! Later cozy up to the indoor Woodstove or outdoor Firepit. Catch up on your fav programs w/Roku TV or play Super Nintendo. Enjoy the newly renovated therapeutic rainfall shower.

Value · Location · Parking

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 🔌 OPEN TIMESLOTS AUGUST 17 (today)-19 (2 nights/3 days) AUGUST 21-23 AUGUST 28 (1 night)

Family · Location · Heating

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.

Location · Value · Barbecue

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.

Location · Value · Wi-Fi

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 :)

Location · Value · Sleep quality

Brookside Cottage - Charming Rural Getaway Mulmur

Our cozy guest house, situated in the Headwaters region, has it all! Close to hiking,golfing,biking,skiing. XCski/snowshoe from your door! Big skies for astronomers and astrophotography! We offer 32 acres of forest and fields for walking and taking in the magnificent views. The area boasts fine restaurants, boutiques, markets and artisans. Minutes to Mono Cliffs, Boyne, Mansfield Ski Club and easy driving to Blue Mountain and Wasaga Beach. Ideal for couples, solo adventurers or a small family.

Family · Location · Indoor spaces

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.

Value · Location · Heating

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.

Family · Location · Amenities

“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”

Value · Location · Kitchen

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*

Value · Family · Nearby

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.

Family · Value · Hiking

Tiny Home retreat in quiet neighbourhood

Keep it simple at this peaceful, centrally located place. Walking distance to: ~ Elora’s shops ~ sites/ attractions ~festivals ~trails The stocked kitchenette includes: ~Small fridge ~Sink ~Microwave ~Hotplate ~Kettle ~French press for coffee ~toaster ~small blender ~All dishes and cutlery ~EVOO, Vinegar, Salt, pepper, sugar, assorted tea, Regular and decaf coffee Also: ~New Double Bed Mattress (Mar 2025) ~Private patio & seating area ~Free Parking ~Wifi

Family · Value · Getting around