Family-friendly holiday rentals in Halton Hills

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.

Spacious 1BR Loft • Well Equipped • Super Walkable

A bright and stylish urban loft in the heart of downtown! This sun-filled suite features soaring 12-ft ceilings, stunning floor-to-ceiling windows, and sleek hardwood floors. Relax on the oversized sofa, dine at the modern table, and cook in the fully stocked kitchen with stainless steel appliances. Sleep soundly on a plush Westin Heavenly queen bed, and refresh in the spa-like marble bathroom. Includes in-suite laundry, high-speed Wi-Fi, and an unbeatable location near vibrant King Street West!

The Trails Retreat (Private Cabin)

Beautifully renovated 2-story private hilltop cabin for romantic getaway, family stay or friends' retreat, experience a taste of the country together. Backed by forest and trails and set away from our family home, minutes to the Bruce Trail, Hockley Ski & Golf Resort, Mansfield Ski Club and charming Orangeville. Enjoy total guest privacy & spectacular sunrises. Guests are welcome to share our heated pool in season:) Add a playful Yoga/Functional Movement class or chef's dinner to your stay!

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

Beautiful 1 Bedroom Apt Steps to Hamilton's Best

Newly finished spacious basement with 8' ceilings and plenty of natural light! Perfect for a romantic getaway or for mature professionals on business. Steps to Locke Street's dining and shops, as well as parks, hospitals, and downtown Hamilton. Features include in-floor heating, 55" 4k TV, a custom kitchen, and laundry. Sleeps 4 with Queen bed in bedroom and pull-out Queen mattress in the sitting room. Free street parking and anytime self check-in.

Charming Cozy Stay | Breakfast & Near Breweries

Settle into a clean, cozy, self-contained apartment with a private entrance in a charming century home. Start your morning with farm-fresh eggs and ready-to-bake croissants. The fully equipped kitchen includes essentials like oil and spices for easy home-cooked meals. Relax in your private courtyard or unwind by the electric fireplace. Just a 2-minute walk to great breweries and a coffee shop, and a 15-minute walk (or 4-minute drive) to downtown.

The Carriage House @ Mingle Hill Farm

Welcome to your relaxing escape on our organic lavender and herb farm, nestled on the scenic Beamsville Bench. Unwind with a glass of local wine on your private deck, stroll through fragrant gardens, or explore the nearby Bruce Trail. Just minutes from 40+ wineries and top dining spots. Only 30 minutes to Niagara Falls and 45 to Niagara-on-the-Lake. A peaceful retreat perfect for nature lovers, wine enthusiasts, and romantic getaways.

Dew Drop Inn

Welcome to your temporary home away from home! Separate apartment within our home (930 square feet). Separate entrance with large foyer. Two bedrooms, 1 with a queen bed and kitchen, the other with a queen bed, futon and T.V. (sitting area). Three piece bathroom with step-in shower. Tons of parking. Hardwood floors throughout. Spectacular views and 2 firepits to use. Please see pictures. No pets allowed.

Lively 1+1 Lakeview Condo near CN Tower + Free Prk

Enjoy the stunning lake view in this open concept 700 sq ft condo with 9 ft ceilings, in the heart of the harbourfront. Right next to CN Tower, Rogers Centre, and Scotiabank Arena. Includes parking space, TV, and internet. Gym, indoor-out door pool, Variety of restaurants and grocery stores steps away. Minutes walk to subway, Union Station, the business district, and Billy Bishop City Airport.