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Best Ofs Toronto

Best Group Getaways

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Picton

The Clarke Road Retreat
Starting at:
$410 per night
Sleeps:
16
Bedrooms:
8

Why We Love It:

Got a group getaway on the docket? The Clarke Road Retreat is one of the biggest Good Weekend-approved spots in the County, with sleeping space for 16 in 8 bedrooms. And with two kitchens, two living rooms, two bonfire pits, and one super-sweet cedar sauna, it’s the perfect layout for big groups that want to hang out together, but also want their personal space. Wifi, flatscreen TVs, and a killer games selection (Rock Band! Mario Kart! Board games aplenty!) make this the ideal retreat for friends or families looking to blow off steam.

Bracebridge

The Leonard Muskoka
Starting at:
$450 per night
Sleeps:
11
Bedrooms:
4

Why We Love It:

If a Muskoka cottage and boutique Toronto hotel had a baby, this Leonard Lake lodge would be that baby. Eight beds sleep 11 guests, all who are sure to be wowed by the cedar barrel sauna, boathouse-turned-hangout, smart tech setup (including virtual assistant speakers and voice-enabled lights), light-filled sunroom and idyllic lake. Perfect for summer vacations and fall getaways.

Picton

The Ferg
Starting at:
$200 per night
Sleeps:
12
Bedrooms:
3

Why We Love It:

Take your pick of three suites at The Ferg, a Picton heritage home that’s been reborn as a farmhouse chic getaway. The one-bedroom-plus-sleeper-sofa unit and the two-bedroom suite each sleep four, while the two-storey Loft — formerly a horse stable — sleeps two in a king bedroom. Whichever you choose, you’ll enjoy Scandinavian-antique vibes and easy access to the county’s wineries, eateries, and beaches.

Drag Lake

Colin and Justin's Lakehouse
Starting at:
$680 per night
Sleeps:
12
Bedrooms:
3

Why We Love It:

Design duo Colin and Justin transformed this all-season property from lacklustre lodge to luxe lakehouse on season three of Cabin Pressure. Now you and 12 friends can reap the many rewards; namely, an outdoor hot tub and sauna, bathrooms with heated floors, a wood-fired oven and smoker, six cabin-chic bedrooms and 173 feet of of private, swimmable shoreline.

Prince Edward County

The Carrington
Starting at:
$989 per night
Sleeps:
10
Bedrooms:
5

Why We Love It:

We’re calling it: The Carrington is one of the best-appointed spots for groups in the County—with the hero feature being its pristine backyard pool, decked out with coral lounge chairs for prime ray-catching (SPF-drenched, of course). Hammock swings, corn hole, and a multitude of indoor and outdoor dining areas make it the perfect spot to post up and stay awhile with a group of couples, or even a bachelorette weekend. Plus, it’s a great price for the area: come with a group of 10 friends, and you’ll each only pay $50 a night. Not too shabby-chic, right?

Highlands East

The Bear Stand
Starting at:
$1,133 per night
Sleeps:
10
Bedrooms:
4

Why We Love It:

Reasons to stay at the Bear Stand: It sleeps 12 of your pals. It’s on 99 acres of ultra private, ultra beautiful waterfront property. It was photographed for Architectural Digest, so Instagram photo opps are guaranteed. It has a Japanese-inspired outdoor soaking tub, a Finnish-inspired indoor sauna, and a six-person, four-season hot tub. Convinced?

Picton

Cressy House
Starting at:
$2,267 per night
Sleeps:
12
Bedrooms:
6

Why We Love It:

Chef Grant van Gameren—the hotspot-making restauranteur behind Bar Isabel, Bar Raval, and Rosalinda—owns this gorgeous retreat in prime PEC wine country, and he’s opened its double-doors on Airbnb for weekend and weeklong rentals up to 14 people. With a pool overlooking Lake Ontario, six sprawling acres of private property (and 500 feet of swimmable waterfront), a Chardonnay vineyard on the property, and Call Me By Your Name-worthy courtyards for lounging with a good read, Cressy is one of our favourite spots for a family vacay or group getaway.

Carling

The Modern Georgian Bay
Starting at:
$1,200 price per night
Sleeps:
7
Bedrooms:
3

Why We Love It:

This architectural beauty for six sits by calm, secluded Georgian Bay waterfront, surrounded by 24 acres of tranquility. Once you’ve had your fill of swimming, kayaking and hiking, move inside to enjoy Marie Kondo-approved minimalism, state-of-the-art appliances and light-drenched spaces. The rocky outcrops and pine trees are even prettier when covered in snow; in-floor heating and a Stuv fireplace will keep you toasty.

Godfrey

The Frontenac
Starting at:
$550 per night
Sleeps:
10
Bedrooms:
4

Why We Love It:

The 700 feet of private waterfront and surrounding raw forest at this sun-drenched Thirty Island Lake retreat make for a great escape at any time of year. The barrel sauna with panoramic views of the bay tops a long list of goodies that include Endy mattresses and Pendleton blankets in all four bedrooms, and Netflix, Nintendo and ping-pong in the living spaces.

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