Guesthouse holiday 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 :)

Adorable Guesthouse Apartment With Free Parking

This beautiful brand new suite offers, Separate private guesthouse with vaulted ceilings & heated floors throughout. Private bathroom with standing shower. Queen loft bed & pull out couch. Flat screen smart TV. Kitchenette which includes: Fridge, cooktop & cookware, toaster oven, kettle, coffee maker. Live edge walnut table with 2 stools. Free wifi. 1 Free parking space. Close to Go Train. Fresh bed sheets & towels are provided. Phone charger and blue tooth speaker. Instagram @blueheronloft

Guesthouse in nature mins to Durham trails & 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 resident ducks! If you are feeling more adventurous, enjoy a hike on our private onsite trail or on one of the many local trails within walking distance in the Trail Capital of Canada! Later we'll get the Woodstove lit for you (Dec - Feb). Catch up on your fav programs with Roku TV. Enjoy the therapeutic rainfall shower guests rave about!

Balcony House 30% off monthly with free Parking

Enjoy the glamour of this spacious, stylish, worry free, upscale place. It is brand new and located in the Heart of Richmond Hill, walking distance from David Dunlap Observatory Park, Plazas, Malls, Schools, Restaurants and Supermarkets. Close To Highway And Go Station, Viva, Yrt. Separate entrance and all inclusive with 1 queen bed, 1 double Sofabed if more than 2 guests, 65in smart TV, high speed wifi. Micro oven, Fridge, K-cup coffee machine, full bathroom, patio sittings, 1-2 free parkings

Warnica Coach House

Welcome to the Warnica Coach House! This unique and historic property will not disappoint! Built by George R. Warnica in 1900, this spectacular property was the recipient of the Heritage Barrie award in 2018. The Coach House where you will stay, once housed horses and carriages, has been completely renovated top to bottom in 2023 with the finest touches. We are centrally located with a 30 second drive from the 400, and an 8 minute walk to the waterfront, restaurants, and downtown fun.

Bosco Hilltop Hideaway

A unique, newly renovated guesthouse nestled on 5 acres ,surrounded by trees with a private walking trail. Just 10 minutes from Niagara Falls and Niagara on the Lake!! 2 minutes to the Niagara Wine Route and many restaurants, wineries, and shopping. Right off the 405, from Toronto and 2 minutes from the Queenston Lewiston Border. Modern farmhouse charm and decor throughout this open concept one bedroom guesthouse. A perfect retreat to relax, restore and explore Niagara.

Beautiful Studio Cottage • Urban Retreat Guelph

Experience an independent, private, sparkling clean studio close to downtown Guelph with full amenities. Located in a gorgeous tree-filled 200 ft backyard, this cozy urban cottage has a comfortable double bed with new mattress, gas fireplace, fully stocked kitchen, separate shower, 2-piece washroom, sleeping loft, and private back patio. Located in the heart of the Junction Village intentional community, guests can connect with others, or have a private retreat experience.

Zorro Guest Suite • Central, Cozy & Private

Newly built cozy attached guest suite w/ private entrance. On a cul-de-sac in a quiet area, yet centrally located. Acoustically insulated for a quiet nights sleep. * 15/20 minutes to YYZ Airport & 5 minutes to Square One shopping center. * 30 minute drive to Toronto * 1 hr drive to Niagara Falls. * Ideal for traveling couples or a solo professional. * Garden views from indoors and from a designated outdoor patio space. * 1 parking spot available in our driveway.