Family-friendly holiday rentals in Caledon

Private oasis in Erin.Hot tub & Woodburning sauna.

WOOD BURNING SAUNA & HOT TUB⭐️ONE OF A KIND, 1800 sq. ft BARNDOMINIUM on 18 acres of total privacy! Serene, country getaway in the picturesque countryside of Erin⭐️Full-size kitchen,harvest table,spotless bathroom, couch & chairs set infront of the floor to ceiling glass doors⭐️Cozy loft with tv, comfy queen bed & oversized couch. ⭐️Soaring trees & trails,grain bin bar on concrete pad with fire-pit, tables & chairs.Wood deck with patio set.Separate cabin with double bed. You won’t want to leave!

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 :)

HotTub & Cozy Fireplace - 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!

Tranquil Tiny House Retreat 4-Season Radiant Floor

Take it easy at this unique cabin experience in the city. The Tiny House is a private 9’ x 12’, fully insulated, 4 season cabin with a couch, kitchenette with running water, queen bed, Loftnet hammock & outdoor shower. Enjoy the natural beauty of our half acre tree-filled backyard, yet still close to downtown Guelph. This is a glamping experience that requires appreciation for tiny house living. Guests have access to a separate portable washroom, by walking about 100ft to the back of the yard.

The Clayhill Bunkie

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

Studio Apartment

Discover the perfect blend of comfort and convenience in this cozy studio apartment, ideally situated in the vibrant heart of Caledon. Key Features: Prime Location: Steps away from shops, cafes, and parks. Modern Amenities: Spacious living area, and stylish bathroom. Natural Light: Large windows that fill the space with warmth and brightness. Community Vibe: Enjoy the friendly neighborhood atmosphere and local events. This peaceful retreat, offers everything you need. Don't miss out!

1850 Settler's Cabin in Private Forest

Our beautiful 1850 settler's log cabin is simply furnished and does not have plumbing. Electricity is powered by a honda generator. Fresh drinking water is supplied. Bathroom is a clean, private outhouse and guests have access to our centralized guest shower facility on premises from 6-9 am/pm daily. As your Bed and Breakfast host we will personally greet you and check you in and always remain on property while offering you privacy. We are designed for a quiet, peaceful rustic getaway.

Hockley Haven

Kick back and relax in this calm, stylish space. 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.

Halton Hills Hideaway_Private Suite

🌿 Halton Hills Hideaway – Cozy Basement Suite Near Downtown Georgetown ✨ What You’ll Love: 🚪 Private Basement Suite – Separate entrance & no shared areas 🛏️ Queen Bed – Comfy and perfect for solo travelers or couples 🌳 Garden Views – Enjoy calming green views from your lookout window 🧼 Clean & Cozy – Thoughtfully prepared for a peaceful stay 🏘️ Charming Neighborhood – Quiet, friendly, and safe 🔍 Check the amenities section for full details—we’d love to host you!

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.

Winter Escape Tropical Dome! Animal Lovers Dream

Jungle Dome on a farm in Burlington! Enjoy a tropical stay in our 500 square foot geodesic dome “glamping” greenhouse dwelling! Sleeps 4. Complete with a fish and turtle pond and filled to the brim with tropical plants! Designed to be a tropical vacation getaway when you can’t get away to the tropics! Situated on a 5 acre animal farm where guests can feed and interact with goats, horses, highland cows, sheep, pigs and poultry. An Animal Lovers Dream!

Garden Studio Apartment

Enjoy a stylish experience at this centrally located place. Newly renovated 1 bdrm walkout apartment located in our home in downtown Orangeville. Steps to Theatre Orangeville, Orangeville farmers market, and Jazz & Blues Festival. Enjoy evenings on your own patio in a private backyard overlooking the garden. Enjoy walks on the Island lake Conservation Park.. Dine at any of the many fine restaurants or cook at meal in your own fully equipped kitchen.