Family-friendly holiday rentals in East Gwillimbury

Four season glamping dome under the stars

Whether you are looking for a romantic getaway for two, a solo remote work week in solitude surrounded by nature, or a family adventure, this 4-season geodesic dome is just the right place. Explore picturesque trails of Scanlon Creek Conservation Area, enjoy inground pool in summer, experience breathtaking sunsets over the farm fields, the starry skies by the bonfire, mesmerizing dance of fireflies in June, and let the frogs and crickets lull you to sleep in the place where time stands still...

Guesthouse w/Woodstove in Nature Near 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 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.

Bed of Roses Airbnb. 45 mins N of Toronto. Hot tub

*Requests typically replied to within 15 mins during the day.* Private bright 2 bedroom basement (sleeps 4 & no shared areas), 45 minutes N of Toronto. We live in a safe neighbourhood, in a home which backs onto a forest. Walking distance to a train station and a very large mall. You will have two private bedrooms, your OWN bathroom and full kitchen, 3 fireplaces, internet & HOT TUB! Separate entrance. No parties. No instant booking. We screen our guests as we live upstairs with our kids.

Stylish, Modern 2nd Floor Private Apt. Quiet Area

Located in a beautiful and quiet neighborhood, this modern apartment can make for a perfect peaceful getaway no matter the occasion. Close to Lake Simcoe, beautiful beaches for swimming & fishing, and plenty of nature trails. Highlights: Large and cozy bedroom with ample storage and work space. Beautiful open concept dining area and kitchen with everything you need. Keurig coffee, tea and some snacks provided. Comfy sofa in front of a large screen TV with Netflix. High speed internet provided.

Adorable Entire Suite,Sep. Entry,1 Parking

Enjoy easy access to stores, restaurants and entertainment from this perfect location. Only 5 min. drive to GO Train & Bus Terminal with quick, convenient transport to Downtown Toronto, Canada’s Wonderland, etc. This lower level guest suite is fully equipped with own laundry, kitchenette with mini fridge, Induction 2 burner Cook Top Stove, microwave, toaster and coffee maker. Cozy Fireplace, 60” screen HD TV and Luxurious King Size Bed Safe Neighbourhood with walking trails and parks.

Place You Want To Stay at With Tons of Options ! !

Brand New, Modern & Open Concept Basement Unit With 9 ft Ceilings & Brand New LG Appliances, Located at Bathurst & King Street In Richmond Hill. Beautifully Decorated & Fully Furnished For Your convenience, Making it a Comfortable Stay - Min walk to Community Park With Playground For The Kids - Min Drive From Lake Wilcox & Bond Lake + Many Other Trails - Tons of Different Variety Of Restaurants - Grocery Stores - Multiple Gyms Close By - Coffee Shops - Public Transportation and Much More

The Hilton BnB Adult Luxury Suite

Experience the elegance of the Hilton BnB nestled in Newmarket’s prestigious Stonehaven Estates, just 30 minutes from downtown Toronto. This beautifully decorated open concept walkout suite in a two-story home offers unparalleled comfort and amenities for 1-2 adult guests. Indulge in dining by the fireplace during winter or unwind with a poolside BBQ in the summer amidst breathtaking grounds. The suite boasts spaciousness and a uniquely designed interior that exudes luxury at every corner.

Private Loft w Sauna, Fireplace, Wi-Fi & Projector

Welcome to the LOFT - A private, eclectically designed spa-inspired unique stay in the historic Webb Schoolhouse, less than an hour from Toronto. Featured in TORONTO LIFE in 2021, this private loft includes a sauna, unique hanging bed, wood stove, kitchenette and is filled with art, and huge tropical plants as well as a projector & giant screen for epic movie nights. Relax and recharge, roam the grounds and enjoy the beautiful outdoor spaces, the permaculture farm, animals, and fire pit.

Deerleap Glamping Dome

Located close to the city, our four-season glamping dome offers a peaceful and unique escape. In winter, the snow-covered landscape creates a magical scene, while inside, the wood pellet stove keeps the dome exceptionally warm and cozy. Nestled on 10 acres of picturesque land and a stunning pond view, Enjoy everything you need—from upscale sanitary facilities to fast Wi-Fi. Whether you’re celebrating a birthday, an anniversary, or simply seeking quiet time in nature.

Cozy apartment in Newmarket

This cozy home, located at Leslie and Mulock, is within walking distance of parks, grocery stores, and restaurants. It’s a short drive to Southlake Hospital, Historic Downtown Newmarket, the GO station, and Upper Canada Mall, Walking distance to Pickering College. Guests have full access to the first floor, featuring a living room, kitchen, dining room, and a private basement apartment, with a private bathroom. Perfect for a comfortable and convenient stay.

Orchard cottage, experience the farm in the city

Beautiful country home nestled in an apple orchard surrounded by nature with private access to walking forest trails and set back off the road with beautiful idyllic views. Close to highway 404 and to all amenities-Walmart, Best Buy, etc. 45 min to downtown Toronto. Property has friendly dogs. **discount for 5 guests or more on a long-term stay. Response time up to 3 hours. Town of Stouffville appoved short-term rental permit # is PRSTR20250480

The Quiet Retreat

Welcome to our cozy suite, your perfect private retreat. Soft beige walls and warm lighting create a comforting atmosphere in our open-concept space. Unwind in the sleeping area or kick back in the living and dining areas with a good book or work. Our separate entrance ensures complete privacy, allowing you to come and go as you please. Make yourself at home in our warm and inviting place, your home away from home. License #BL2023-00257