Airbnb and Other Home-sharing Companies Have Landed in Headwaters
Here’s how to find the log cabin, country estate or yurt of your dreams – for at least one night.
Overnight visitors to the hills of Headwaters can rest their weary heads on a wide range of beds for hire, from upscale retreats such as the Millcroft Inn and Hockley Valley Resort to a diverse list of charming bed-and-breakfasts on main streets and rural routes. Now, with the rise of Airbnb and other home-sharing services, a new crop of options has sprouted for those hunting for getaways off the beaten path – sometimes so far off they don’t even have hot water.
From tiny rustic boltholes tucked away in the woods to country manors ready to host bridal parties, these new retreats are designed to woo all manner of tourists, as well as local folks with friends or family in need of a place to stay for a wedding, sports tournament or business meeting. Once introduced, locals may consider signing on for a getaway of their own – minus the travel time. Ever wondered what it would be like to live in a yurt or a log house? Renting one nearby might help you decide.
Homeowners are opening their doors for a number of reasons beyond making a little money. Some just aren’t using their entire property. Others have the bed-and-breakfast itch, but don’t want to make a full-time commitment. And still others thrive on meeting the revolving cast of characters who come to stay. “It’s a certain kind of personality who goes the Airbnb route,” says Kelly Doyle, owner of Mulberry Manor in Mono. “Guests are a bit more adventurous, open to new experiences, and we tend to get along famously with them.”
We searched out a few of the more intriguing options in our midst. Here’s what we found.

A misty morning at one of the most peaceful home-share rentals in the region. The oldest part of the home is the original 1840s log farmhouse. Courtesy Malcolm Roberts.
Farmhouse fun
As you drive up the secluded lane, through an archway of majestic trees, you soon realize you’re arriving somewhere special. The entire property exudes peace, beauty and a true sense of escape. It could be the welcoming feel of the log farmhouse itself, with its ample sitting rooms, two-foot-wide original floorboards, claw-foot tub and chic linens. Outside, there’s a hot tub, outdoor shower, substantial al fresco dining area and trees that whisper in the wind. Kids will go nuts for the barn swing, tree house, playground structure and neighbouring horses. Malcolm Roberts is the old-school host, amenable to chat or adept at making himself scarce. “That’s the beauty of a century home with two staircases,” he notes. “Besides being perfect for an epic game of tag, it allows me to slip down to the kitchen and out to the grounds without disturbing anyone.”

One of the sunlight-filled bedrooms at Malcolm Roberts’ farmhouse rental. Courtesy Malcolm Roberts.
location
Near Highway 89 and Airport Road
size
Four bedrooms, four beds; sleeps up to seven
cost
From $335 a night
choose this one if
you and the family would love to visit the fictional Sunnybrook Farm
book it
A garden paradise
It’s easy to see why Longwood Cottage, the two-storey private wing of a country house, is popular with bridal parties getting ready for the big day. In addition to the clean, minimal Arts-and-Crafts-style décor, amazing gardens provide a spectacular setting for photos or quiet pre-wedding contemplation. Herbs from the gardens, along with eggs from the resident chickens, tend to make their way into a delicious French omelette breakfast delivered to guests’ private kitchen. Another enticement is the local cycling. Hosts Paul and Melinda Flach will pack you a box lunch for the road. And in the winter more than 10 acres of land make for great snowshoeing and there’s skating on the pond.

Lush gardens make Longwood Cottage a popular spot for bridal parties. Photo by Rosemary Hasner / Black Dog Creative Arts.
location
Near Belwood, just over the border of East Garafraxa
size
Three beds, two bedrooms; sleeps six
cost
From $110 a night
choose this one if
you’ve always dreamed of living on a country estate
book it
On golden pond
This lovely tiny cabin nestled in the woods of Mono includes a loft-style bedroom, composting toilet, coffee station and barbecue. “Cabin on the 9” is steps away from a clear, spring-fed, blue-clay pond where you can swim, enjoy the floating raft, paddleboard (if you bring your own) or go fishing. A tented hammock suspended between trees offers a bug-free way to gaze at the stars or read a great book. And if you’re so inclined, yoga lessons are on offer. Breakfast, a full kitchen and a hot shower are a quick jaunt away at the main house, where amiable host Bill Dandie will be happy to point you to restaurants and activities in the area. If you’re making the journey in the winter, stay toasty in front of the wood stove and enjoy the hockey gear, sleds and snowshoes Bill provides. Fun fact: This summer marked the first marriage proposal made and accepted at the cabin – by a couple visiting from Lyon, France.

This rustic Mono log cabin is perched at the edge of a spring-fed clay pond. Courtesy Bill Dandie.
location
Near Highway 9 and 4th Line Mono
size
Two beds, one sofa bed; ideal for a couple
cost
From $144 a night
choose this one if
you want to get away from it all
book it
Village life
Who knew that two beautiful suites sit above the Cheltenham General Store smack in the middle of the charming village in southwest Caledon? Each of the Cheltenham Suites can sleep four, with separate bedrooms and lounge areas flooded with natural light and decorated with crisp, bright paint and furnishings. Butter tarts, fudge and life-sustaining coffee are just a few steps below. There are also other fun finds in the shop, including handcrafted soaps and a free book exchange. Guests also have use of the massive back patio overlooking the Credit River. With the hustle and bustle and delicious flavours of a village shop at hand, you’ll feel as if you’ve stepped back in time, but with all the conveniences expected by today’s travellers.

Sleep at the heart of the quaint village of Cheltenham above its general store. Photo by Rosemary Hasner / Black Dog Creative Arts.
location
Cheltenham
size
Two suites, each 300 to 330 square feet; each sleeps four
cost
From $135 a night
choose this one if
you’ve yearned to visit Stars Hollow, hometown of TV’s Gilmore Girls
book it
Riverside living
Booking assistant Michelle Rodrigues refers to the Nottawasaga River Retreat as a cottage, but it comprises five bedrooms and enough side rooms and sofas to sleep 14 – perfect for a family or business retreat. The spacious lawn is large enough for a game of soccer or football, and a spare room inside is just right for yoga or meditation. But the real draw is the river, which you can hear even when you’re inside. A quick walk down the path and you’re standing on its banks. Now that the annual salmon run is underway, Michelle says she expects the cottage to be fully booked. There’s also a beach chock full of beautiful river rock, perfect for skipping. Hockley General Store is just a few minutes away should you need a treat, ice cream or a delicious frozen chicken pot pie to bake at “home” on the river.

A room for meditation and yoga overlooks this charming spot on the river. Photo by Bob Gundu.
location
Hockley Valley
size
Five bedrooms; sleeps up to 14
cost
From $315 a night
choose this one if
your favourite movie is A River Runs Through It
book it
Glamp it up
If you’ve ever fantasized about living in a yurt, this is your chance to do it style. This large and spotless yurt, set in a secluded forest clearing, features an outdoor fire pit, an indoor wood stove and an attached composting toilet. Stargaze outside or peer up at the skies through the circular window in the top of the structure. Showers and a bathroom are a minute away in the yoga studio attached to the main house. Massages and private weekend yoga classes are on offer during your stay at Soaring Heart Studio Retreat, or you can join one of the regularly scheduled weekday classes. Owners Ellen Brakel and Joey Lemieux can show you where to forage for wild herbs and berries on the property (they use them to produce their Escarpment Teas; see in Made In The Hills) – or you can pop into nearby Shelburne to shop for goodies to cook over the campfire.

Try out life in a simple yurt near this getaway in Mono and take an on-site yoga class if the mood strikes. Photo by Rosemary Hasner / Black Dog Creative Arts.
location
30 Sideroad Mono
size
One double bed, two singles; sleeps up to four
cost
From $65 a night
choose this one if
you crave a digital detox (there’s no power in the yurt)
book it
A hiker’s dream
This bijou cabin boasts a modern kitchen, wood stove, master bedroom with king-sized bed and a killer view. The Trails is the kind of place that’s hard to leave – until you discover hiking trails it’s named for, which lead right from the cabin to a series of waterfalls and connections to the Bruce Trail. Post hike, cool off at the pool, then try your hand at archery. In the main house, host and professional chef Jeff Baker’s kitchen is tailor-made for group cooking lessons. You can also enjoy a private chef-prepared meal in a separate dining room or delivered to the cabin. The other half of the hosting pair is Jill Baker, yoga teacher extraordinaire. Her studio is in a separate building with ample space and serene, minimalist decor. Catch one of Jill’s community classes through the week, or she’ll offer a private class for you or a group. In winter the path to the cabin makes for a great toboggan run, and ski hills are minutes away.

Steps from this quiet log cabin you’ll find waterfalls and hiking trails. Photo by Rosemary Hasner / Black Dog Creative Arts.
location
10 Sideroad Mono
size
One bedroom, one sofa bed; sleeps up to four
cost
From $200 a night
choose this one if
you’re looking for all the amenities, but none of the crowds
book it
Estate ease
Mulberry Manor dates to between 1850 and 1880, with a 16-foot ceiling in the great room, 10-foot French doors, a massive fireplace and lovely antiques. Modern updates include a large kitchen, as well as a swimming pool and hot tub. Hosts Kelly Doyle and her mother, Lee, can book massages or chiropractic sessions in-house. Rooms have been popular with the equestrian set attending training events or competitions, employees on long work assignments, and those looking for a relaxing retreat where they can enjoy the pool and watch for regular visits from wildlife. Kelly has even been known to literally go that extra mile and drive hikers to the Bruce Trail and guests to a wedding. “I’m happy to do it,” she says.

The posh country Mulberry Manor offers amenities to book including massages. Photo by Rosemary Hasner / Black Dog Creative Arts.
location
Highway 9, near Palgrave
size
One king bedroom, one double bedroom, one single bedroom; sleeps up to five
cost
From $99 a night for each room
choose this one if
you pine for a century home.
More Info
So you want to be a home-share host?
You’ve got an amazing property. You’ve got space. You’ve always had a yen to be an innkeeper. To find out if you have what it takes, check out these tips from the hosts we met.
Working with Airbnb
Home rental agencies – from traditional to online, such as Airbnb and VRBO – have different operating procedures. Airbnb, for instance, usually charges a 3 per cent fee for each reservation. As part of their online service, they verify your guests, handle the payment and offer $1 million in insurance. And they outline a host’s responsibility for checking into local laws and bylaws that could affect the rental.
Not sure what to charge? Wondering how to attract more reservations? Airbnb offers advice and encourages hosts to interact online and share what they’ve learned on the ground. “It’s like having a big brother and supportive business partner all in one,” says local host Bill Dandie.
Cleaning up
Yes, this takes time. After every guest’s visit you need to do a full clean, even if they stayed for only one night, explains the crew that tends to Cheltenham Suites. You will wash a lot of linens! And you’ll need to have a backup plan if you’re away during a changeover. Faced with that scenario this summer, Melinda Flach had brainstormed plan B. “If that hadn’t worked out, we’d have had to return early from vacation,” she adds. “It’s all part of the process.”
Communicating with guests
There’s a lot of this. Some hosts choose to split up the duties, dealing with online inquiries via email, for instance, then communicating with booked and current guests somewhat more personally via texting. Technology can also help ensure guests’ privacy and comfort. From afar, for example, Glen Judge can use his iPhone to adjust the temperature of his Cheltenham Suites and to change the digital key code to ensure each guest has a specific, secure code.
Making the rules
Rules help make renting your property sustainable. As much as you’d like to be open-ended and flexible, you aren’t staffed like a hotel and can’t allow for check-in “anytime” or a check-out that doesn’t leave enough time to clean and prep for the next guests, Jill Baker explains. If you’re hosting a bridal party or corporate retreat, be diligent about confirming the number of guests and consider a charge for day guests and extra cleaning. Melinda Flach has learned bridal parties can quickly multiply into a large crowd there to share the excitement. Fabulous, yes, but some guidelines are necessary. And remember, not everyone reads or retains the rules and instructions for the property, so be prepared to repeat yourself and be firm.
Setting the bar
Reviews are very important in this busi- ness, and the owner’s standards must be of the highest calibre. As Grandma used to say, “Good enough never is,” so be prepared to offer the same stand- ards you would expect in a destination. After all, if guests find a property sub- standard, they rarely keep their disap- pointment to themselves. Negative online reviews can scupper your busi- ness for weeks and months to come.
Getting noticed
It can be hard to stand out, Jeff Baker acknowledges. Consider what makes your property unique and use that as a hook. Are there any experiences your property or you as hosts can offer? Guided walks, photography lessons and massage therapy are all good bets. Both Bill Dandie and Ellen Brakel paired their remote retreats with massage therapy and yoga, and Jeff Baker’s cooking lessons are a great example of adding an extra incentive.