10 fantasy summer cottage rentals within a four-hour drive of Toronto

A cottage isn't a cottage without a horse stable, a duck farm, an indoor pool or a Wes Anderson-themed decor

My favourite way to deepen or renew a connection with a person is to go on a road trip with them.

A long drive is the perfect excuse to have big talks or check out new podcasts or play each other your favourite album. Even sitting in comfortable silence as you look out the window can make you feel closer to someone by the time you get wherever you are going.

The formula for a successful road trip is simple. Access to car + amazing snack selection + pre-loaded Google Maps + destination = great times.

If you need help on the destination front, here are 10 very surprising rentals within a four-hour drive of Toronto.

Luxury loft with horse roommates

Imagine a dreamy open space with exposed beams, a grandfather clock and a clawfoot tub. Great, right? Now imagine that space above a barn that a bunch of horses and a cat named Marv live in. There are also lambs, sheep, chickens and cats – all of which are treasured by hosts Deborah and Eric. This Airbnb listing comes with the caveat that you make extra sure you know you will be sleeping in a barn with horses, which would be a lousy thing to be surprised by. (There is even a “bale and breakfast” option, if you happen to be travelling with a horse of your own.) This listing gets extra points for making clear that humans of all races, genders and religions are to be treasured too.

Drive time: 1.5 hours

Price: $80 per night

Good for: Remembering there is goodness in the world, reading Misty Of Chincoteague


Source: Airbnb

Converted boxcar cottage

Did you know that there is an Ontario town called Utopia? There is, and you can go there and live in a boxcar. This Airbnb is parked on the grounds of a farm owned and operated by a woman named Vera, who is a “kundalini yoga teacher, life coach, writer, florist, cooking, gardening, environmentalist, mycologist and herbalist.” The cottage itself is lovely (it has a wood stove), and there is an indoor pool attached to the house that guests are welcome to use.

Drive time: 2 hours

Price: $169 per night

Good for: Reliving your train-jumping youth in bougie style, developing five new healthy habits at once


Source: Airbnb

Wes Anderson Dream Home

This place will either make you want to throw up or clutch your heart – there is no in-between here. Host Dayna has decorated each room based on a different Wes Anderson movie, and I’m afraid if I ever went there I would be physically unable to leave. If for some reason you did want to venture outside, Prince Edward County has cafes, antique shops and the Sandbanks to explore.

Drive time: 2.5 hours

Price: $224 per night

Good for: Wes Anderson movie marathons, hanging with a friend who is getting over a breakup


Source: Airbnb

The twee-est shed on earth

The bad news: this place doesn’t have a bathroom. (You have to use the one in the main house.) The good news: it’s the perfect retreat for those of us who sometimes just wish we could cocoon in an adorably cozy tiny space. If you get claustrophobic, you can wander the grounds of what the host calls a “castle.” (It’s more of a mansion.)

Drive time: 2 hours

Price: $99 per night

Good for: Small-to-medium makeout party, knitting a tiny sweater


Source: Airbnb

Swingin’ small town church

Much like the Wes Anderson Dream Home, this is the sort of place you will love or hate. A lot of people feel weird about being in churches, which is completely reasonable. But if stained glass windows and high ceilings are your jam, you could certainly do worse than a place that also has an indoor swing set.  

Drive time: 2 hours

Price: $274 per night

Good for: Wedding photography, processing church-related emotions


Source: Airbnb

Industrial fairy tale cottage

The sum total of what I know about Orangeville is contained in this Airbnb listing, so I’m pretty sure the town is a magical Pinterest board come to life. This tiny house has a babbling brook in the backyard, a loft sleeping space accessible by ladder, and is decorated with a combination of antique velvet chairs and contemporary squirrel pillows. It doesn’t sound like it should work, but it does.

Drive time: 1.5 hours

Price: $144 per night

Good for: Nature adventures for grown-up indoor kids, writing retreats


Source: Airbnb

Detroit’s best urban duck farm

When you think of staying in Detroit, you might picture a giant loft or cool art deco apartment in a converted hotel. Those types of places have a lot going for them, but what they don’t have is a bunch of ducks living in the backyard. In addition to the ambient quacking, this house also has quaint decor, a chalkboard wall and a wood stove.

Drive time: 4 hours

Price: $105 per night

Good for: Hanging out with ducks while eating Windsor Pizza


Source: Airbnb

Moderately creepy converted school

You know that episode of Fringe where Olivia, Peter and Walter go back to the Jacksonville school where (spoiler alert!) Walter conducted experiments on Olivia when she was a child? If not, then this place is super-charming and not at all the stuff of nightmares. Somehow it looks both like a horror movie set and a spread in Real Simple Magazine.

Drive time: 2.5 hours

Price: $250 per night

Good for: LARPing, reminiscing about grade school

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Source: Airbnb

Indoor pool and hot tub thrills

I never expected a house in North Bay to become one of my favourite places on earth, but here we are. This otherwise perfectly normal house just happens to have a giant room off the kitchen with a huge indoor pool and a regular-sized hot tub. If you want to spend every day swimming but hate interacting with strangers, this just might be your favourite place, too.

Drive time: 4 hours

Price: $185 per night

Good for: Mermaid slumber parties, exceptional Snapchat videos


Source: Airbnb

The shiniest place you’ll ever sleep

This could be confirmation bias talking, but I’m pretty sure every person dreams of spending at least one night in an Airstream trailer before they die. This place is chrome-and-Formica heaven, with the added bonus of being parked on the lawn of what I’m assuming is Sundridge, Ontario’s nicest resort. So after you admire your face in every surface, you can chill in a lodge with antlers all over the place.

Drive time: 3.5 hours

Price: $136 per night

Good for: Creating a retro-futuristic video game, watching any season of The Golden Girls

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