Smoking friendly holiday rentals in Simcoe County

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

*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.

Serenity, Simplicity and Stone

This is a tiny cottage in a sleepy little hollow that opens onto the Georgian Bay. Inside, each stone was carefully chosen and the woodwork was built, piece by piece, by two craftsmen who are highly skilled and passionate about repurposing. It's an art that will leave you in awe; especially if you're worried about climate crisis. The coat hangers are upcycled 100-year-old railway spikes! If you're looking for luxury you will be disappointed but if you're a minimalist you're going to love it.

Romantic Spa/Sauna Cabin Getaway

This unique 'off grid style' is a tiny cabin surrounded by nature & panaramic views. Hosted on the lands of WÄRME Wellness- A SPOT TO RETREAT, relax & endure much needed downtime : by yourself, a couple/ two family members/friends who are looking for spa quality time 'away from it all.' Inside - enjoy the benefits of sauna/spa culture w/ an authentic large wood powered sauna. Bathrooms are located adjacent to cabin. Yoga studio available for rent. Ask about our ‘elevated romance package.’

Accessible Luxury Riverside Beauty!

Welcome to your dream getaway on the serene Severn River — a completely renovated, designer-owned home created with love by a mother for her quadriplegic son. Every inch of this stunning space was reimagined to be both fully accessible and breathtakingly beautiful — a seamless blend of function and style where you’d never guess a wheelchair was part of the design. Enjoy panoramic views of boats gliding by from nearly every room, or unwind on the expansive deck as the sun dances on the water.

Quiet Waters Getaway

Step onto this cozy modern cottage tucked away on the waters of Waubaushene Ontario. Drop a fishing line off our 100ft+ dock, or take a paddle on the lake! Warm up next to the fire under the netted gazebo, or roast marshmallows over the second fire pit under the stars. As we move into the colder month’s Mount St. Louie ski hill is a short drive away from our winterized space. Whatever adventure you choose to do, create those memories with your friends and family at our Quiet Waters Getaway!

JJ’s small town country retreat

Take a step back in time to this old farm house. Located on the corner of our little town called Badjeros. This house was built in the 1930s and it’s been in our family for over 80 years. Since then there has been numerous upgrades to the house as well as a large 1200 square foot open concept addition built onto the existing house. While out in the country, this house is central to many attractions in the area 1.5 hours south of Toronto/GTA. Blue Mountain/ Collingwood is 30 minutes north.

Hot Tub & Sauna Retreat by Georgian Bay Trails

Sunset s'mores by the firepit, morning paddling from your doorstep, and evening soaks in your private hot tub—Eagle Point Cottage is where Georgian Bay weekends become unforgettable memories. This modern cottage sleeps 8 (4 bedrooms + heated bunkie), sits steps from the Tay Shore Trail and public beach access, and comes fully equipped with a sauna, kayaks, canoe, and board games. Superhost Stephen averages 4.83 stars across 185 guest reviews. Ready? Reserve your dates today.

Luxe Modern Retreat - Theatre, Hot Tub and Bar

Welcome to an extraordinary luxury home in Orillia - a rare, fully upgraded designer home intended to deliver an unforgettable five-star experience. This is not your typical Airbnb. Every inch of this home has been thoughtfully curated with premium finishes, high-end amenities, and entertainment-focused features. So whether you’re planning a weekend getaway, family retreat, or group experience, this property delivers a true five-star atmosphere.

Studio Bunkie near Bruce Trail!

This is a 9’x11’ hut fit with a sofa couch, small table, and a couple of chairs. Nothing fancy just a peaceful get away back in the middle of a field on a 100 acre property. We also have a supply hut with two single air mattresses and a double air mattress with battery operated pumps to pump them up. The hut also contains staple items such as extra toilet paper, paper towels, batteries, fire wood, coal for coal BBQ, etc.

Modern 6BR Retreat in Horseshoe | Pool + Hot Tub |

Gather your family, friends, or colleagues for the ultimate Horseshoe Valley escape. This 6-bedroom, 3-bath modern retreat features a pool, hot tub, fireplaces, and two living spaces for relaxation and entertainment. Perfect for family reunions, group getaways, or business retreats, the home offers bright interiors, stylish finishes, and thoughtful touches, all close to nature and top local attractions.

Private Log Cabin with 7 beds, 2 futons + hot tub

Forget your worries and enjoy the beautiful nature and the variety of wildlife in this spacious and serene space. Enjoy the outdoor shower on hot summer days. taking in the amazing night skies, perfect for star gazing in or out of the hot tub. Creemore and its brewery are close by, we're not far from Wasaga Beach or Blue Mountain and Collingwood so there's something for everyone and all seasons.

3 separate sleeping rooms on 23-acre horse farm

Self-contained lower unit on 23-acre horse farm. Sleeps 6, fully equipped kitchen, laundry facilities, separate entrance, internet, TV streaming. One full bathroom, outdoor sitting area, parking for 2 vehicles. Owner on premises. 15 minutes east of Orangeville. 10 minutes to Palgrave. 15 minutes to Hockley Valley Resort and 30 minutes to Mansfield. Minimal 2 nights. Discount for week.