Booked Winter 2027

By The Bay

Chalet in The Blue Mountains, ON
5.0
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 10
  • No pets
C$1,677 to C$1,799 per night
incl. taxes and fees

BY THE BAY AREA This beach chalet is steps from the Georgian Trail where summer biking, hiking and winter snowshoeing enthusiasts can enjoy 34 km of trails. Head into Thornbury Village and take in quaint shops, fine dining, or grab a locally crafted cider. Blue Mountain private ski clubs (Georgian Peaks, Alpine, Craigleith and Osler Bluffs ski clubs) and The Village are a 10 minute drive for more shopping, dining and outdoor…

Mystical Bluff

Chalet in Gibraltar, The Blue Mountains, ON
5.0
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 10
  • No pets
C$1,659 to C$1,780 per night
incl. taxes and fees

MYSTICAL BLUFF AREA Nestled in the woods just outside of Gibraltar, Mystical Bluff sits atop the Osler Bluffs in the town of The Blue Mountains. Directly across from the property is access to the Bruce Trail System, known to locals as "3 Stage" or the best mountain biking spot! Enjoy hiking, golfing, beaches along the shores of Georgian Bay, snowshoeing, cross country skiing and snowmobiling. Just down the road is Pretty River…

Sun and Ski

Chalet in The Blue Mountains, ON
  • 6 Bedrooms
  • 4 Bathrooms
  • Sleeps 14
  • Pets allowed
C$1,670 to C$1,791 per night
incl. taxes and fees

SUN AND SKI AREA This four seasons 6 bedroom, 4 bath home is minutes from beaches on Georgian Bay and hiking, biking and mountain bike trails including the Georgian and Bruce Trails. The local ski clubs including Blue Mountain Resort and Village are also within minutes. Nearby historic and charming Collingwood and Thornbury with their specialty shops, restaurants and galleries, Scenic Caves Nature Adventures, the Scandinave Spa, and a variety of vineyards,…

Booked Winter 2027

The Base Lodge

Chalet in The Blue Mountains, ON
  • 6 Bedrooms
  • 4 Bathrooms
  • Sleeps 16
  • Pets allowed
C$1,660 to C$1,780 per night
incl. taxes and fees

THE BASE LODGE AREA The Base Lodge is in the heart of Ontario's four season playground. Close to all local activities and amenities including Blue Mountain Village, all the private ski clubs, The Georgian Trail, beaches along the shores of Georgian Bay, Scenic Caves Nature Adventures, Scandinave Spa, vineyards, orchards, micro-breweries, and the list goes on. The historic town of Collingwood and charming Thornbury/Clarksburg are just 10 minutes away with their specialty…

Fit to Be King

Condo in Downtown Toronto (CN Tower / King and Spadina / Railway Lands / Harbourfront West / Bathurst Quay / South Niagara / YTZ), ON
  • 2 Bedrooms
  • 3 Bathrooms
  • Sleeps 4
  • No pets
C$948 to C$1,174 per night
incl. taxes and fees

FIT TO BE KING AREA King West is one of Toronto’s most dynamic and fashionable neighbourhoods, known for its vibrant energy, upscale dining, and urban lifestyle. The area is home to some of the city’s most celebrated restaurants, stylish cafés, and lively nightlife, attracting professionals, creatives, and visitors alike. Boutique fitness studios, wellness spaces, and high-end retail further enhance the neighbourhood’s appeal. Located just minutes from Toronto’s financial district and waterfront, King…

The High Life Toronto

Condo in Toronto, ON
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
  • No pets
C$1,015 to C$1,259 per night
incl. taxes and fees

THE HIGH LIFE AREA Stunning penthouse residence in Humber Bay Shores featuring breathtaking lake and city views, expansive windows, and an elegant open-concept layout. Enjoy luxury waterfront living with premium building amenities, parking, and immediate access to trails, parks, and the marina — all just minutes from downtown. PROPERTY THE HIGH LIFE Perched high above Toronto’s coveted Humber Bay waterfront, The High Life delivers an exceptional living experience defined by light, space,…

A Loon’s Lottery

Cottage in Gravenhurst, ON
5.0
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 10
  • No pets
C$1,036 to C$1,832 per night
incl. taxes and fees

A LOON'S LOTTERY AREA Nestled on the shores of Loon Lake, A Loon's Lottery is just minutes away from Gravenhurst with amenities at your doorstep! Spend an afternoon wandering the wharf, home to the Muskoka Steamship's, with an ice cream in hand! On Wednesday's, enjoy the small town Farmer's Market featuring fresh produce and precious products. A Loon's Lottery is only 10 minutes from the Muskoka Bay Golf Club Resort and 20…

A Modern Moose Lodge

Cottage in Port Carling, ON
5.0
  • 5 Bedrooms
  • 7 Bathrooms
  • Sleeps 10
  • Pets allowed
C$3,749 to C$14,056 per night
incl. taxes and fees

A MODERN MOOSE LODGE AREA Located right off Peninsula Road on the west side of Lake Rosseau directly across from Clublink's Lake Joe Golf Club. Prime central Muskoka location with close proximity to many Muskoka attractions, by car or boat! Two minute drive to Port Sandfield and its bakery, butcher, deli ,grocery store and marina! 2 minutes to the Lake Joseph Club and 10 minutes to Port Carling, and less than 5…

A Rosseau Timelapse

Cottage in Minett, ON
  • 7 Bedrooms
  • 5 Bathrooms
  • Sleeps 14
  • Pets allowed
C$4,293 to C$11,376 per night
incl. taxes and fees

A ROSSEAU TIMELAPSE AREA Just minutes from Port Carling with access to shopping and dining, and the town of Rosseau with it's famous farmer's market. PROPERTY A ROSSEAU TIMELAPSE - Front entrance accessed from luxurious private paved driveway that easily parks 8 vehicles. Extensive landscaping, walkway and plantings. Deck with lounge furniture and BBQ, beautiful views on the lake. INTERIOR COTTAGE MAIN LEVEL Professionally decorated by Patton Design. Clean modern high ceilings,…

An English Manor

Cottage in Innisfil, ON
  • 14 Bedrooms
  • 13 Bathrooms
  • Sleeps 31
  • Pets allowed
C$7,236 to C$17,124 per night
incl. taxes and fees

AN ENGLISH MANOR AREA This stunning oasis is located only 1hr 45minutes from downtown Toronto. Positioned on the west side of Lake Simcoe, An English Manor is conveniently located 20 & 24 minutes outside of Innisfil and Barrie respectively. A short boat ride away from Friday Harbour resort - a perfect spot to shop, golf and dine. Arrive at Costco within a 20 minute drive - providing renters with great convenience. PROPERTY…

At Last

Cottage in Gravenhurst, ON
  • 6 Bedrooms
  • 4 Bathrooms
  • Sleeps 11
  • Pets allowed
C$1,718 to C$3,646 per night
incl. taxes and fees

AT LAST AREA Located approximately 2 hours outside of downtown Toronto, this cottage provides renters with incredible privacy and proximity to some of the most popular destinations in the region. Whether you are looking for groceries in Gravenhurst, a nearby golf course, or some amazing restaurants in Bracebridge, all these amenities are just a 9, 14 and 24 minute drive respectively. PROPERTY AT LAST - Arrive at the large parking lot that…

Anchors and Antlers

Cottage in Port Carling, ON
  • 6 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
  • No pets
C$7,344 to C$7,889 per night
incl. taxes and fees

ANCHORS AND ANTLERS AREA Nestled approximately two and a half hours from Toronto, this exquisite cottage on Deer Bay in Lake Joseph offers stunning southwest views. Conveniently situated near the esteemed Lake Joe Club, residents can easily access a variety of recreational activities and leisure opportunities. Additionally, the vibrant downtown Port Carling, known for its charming on-the-water dining options, unique local shops, and essential amenities, is just a short distance away, making…

Auld Lang Syne

Cottage in Port Carling, ON
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 10
  • No pets
C$4,951 to C$9,612 per night
incl. taxes and fees

AULD LANG SYNE AREA Situated just 2.5 hours from Toronto and 10 minutes from Port Carling, this location offers convenience and accessibility. Nestled steps away from the renowned Lake Joe Club, which features delightful dining options at the Bistro, residents and visitors alike can enjoy culinary delights. Additionally, with Port Sandfield only five minutes away, the area provides easy access to a variety of shopping and amenities, ensuring that all essential services…

Avondale

Cottage in Port Carling, ON
5.0
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
  • Pets allowed
C$1,258 to C$2,275 per night
incl. taxes and fees

AVONDALE AREA Cruise down to Port Sandfield for your morning latte or come for a late afternoon ice-cream cone while picking up some groceries at the Silverstream Farms. Take a quick boat ride through the Joe River, one of the entrances to Lake Rosseau's hot spots, within easy driving distance to the JW Marriott, The Rock Golf Club, and more! Boat the Big 3 from this location. PROPERTY AVONDALE - This 100’…

Avonlee

Cottage in Port Carling, ON
  • 8 Bedrooms
  • 7 Bathrooms
  • Sleeps 18
  • Pets allowed
C$9,651 to C$18,550 per night
incl. taxes and fees

AVONLEE AREA Avonlee is located on pristine Lake Joseph in a quiet bay. Just 10 minutes north of Port Carling and 5 minutes from both Port Sandfield and Minett on the prestigious Hemlock Point Road, this is the best of both worlds with peaceful privacy and easy access to local attractions, amenities, and unique shopping destinations. PROPERTY AVONLEE is nestled in the natural backdrop of tall pines with pristine landscaping that creates…

Bal Harbour

Cottage in Minett, ON
5.0
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 10
  • No pets
C$4,399 to C$11,699 per night
incl. taxes and fees

BAL HARBOUR AREA Bal Harbour cottage is located in Wiley Bay on Lake Rosseau. Five minutes by boat to JW Marriott and Clevelands House. Gorgeous lake views and western exposure displaying the perfect Muskoka sunsets. PROPERTY, BAL HARBOUR - As you make your way up to the cottage a new front deck greets you as well as new landscaping at the front entrance. Gorgeous NEW 3 slip boathouse with expansive dock, living…

Balaloma

Cottage in Muskoka Lakes, ON
5.0
  • 7 Bedrooms
  • 4 Bathrooms
  • Sleeps 16
  • Pets allowed
C$1,858 to C$3,553 per night
incl. taxes and fees

BALALOMA AREA This Balaloma cottage could not be more central! One minute outside of Bala, you can walk to town or boat to Don's Bakery! Eight minutes to Port Carling and 20 minutes to Gravenhurst. View of Bala Park Island. PROPERTY BALALOMA is a very nicely appointed and maintained property. Lovely sitting areas and gardens throughout the driveway side and lakeside of this beautiful, deceivingly large, and spacious cottage. INTERIOR MAIN COTTAGE…

New Lower Price

Barefoot Bay

Cottage in Port Carling, ON
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 10
  • Pets allowed
C$4,418 to C$8,571 per night
incl. taxes and fees

BAREFOOT BAY AREA Discover the charming town of Port Carling, just a 2.5-hour drive from Toronto, renowned for its scenic beauty and relaxed atmosphere. Enjoy nearby attractions like Port Sandfield Marina for boating and waterfront adventures, and the Lake Joe Club, offering excellent golfing opportunities for a fun and leisurely day. Whether you're seeking outdoor activities or a tranquil retreat, this Port Carling cottage provides a perfect escape to unwind and explore.…

Bentwood Beach

Cottage in Rosseau, ON
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 9
  • Pets allowed
C$4,532 to C$7,922 per night
incl. taxes and fees

BENTWOOD BEACH AREA Located just 10 minutes from the Town of Rosseau, 10 minutes to the Marriott and 15 minutes to Port Sandfield and 25 minutes to the hub of Muskoka - Port Carling. Peruse the many downtown boutique shops including Red Bean Interiors, Lemonwood, the York & Mason café and L'eau! Down on the boardwalk visit Riot Clothing and Lululemon with an ice cream in hand from Mooskoka's, and then finish…

Big Al’s Sunset Getaway

Cottage in Lake of Bays, ON
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 10
  • No pets
C$4,724 to C$9,645 per night
incl. taxes and fees

BIG AL'S SUNSET GETAWAY AREA Nestled in a magnificent rock cut on the northern shores of desirable Lake of Bays, Big Al's Sunset Getaway boasts unmatched, pristine views! Minutes from the small town of Dwight where Erika's bakery and Henrietta's bakery both offer daily baked goods. On Wednesday's enjoy the Dwight farmer's market where local artisans proudly display their artifacts. Alternatively, the town of Huntsville is only 30 minutes away where you…

Big Chill

Cottage in Bracebridge, ON
  • 5 Bedrooms
  • 7 Bathrooms
  • Sleeps 12
  • No pets
C$4,664 to C$9,052 per night
incl. taxes and fees

BIG CHILL AREA Located in beautiful Ennis Bay on Lake Muskoka. Only 10 minutes to Bracebridge and 15 minutes to Gravenhurst. Less than 2.5 hrs from Toronto. PROPERTY BIG CHILL, a stunning, brand new Sheppard Construction build that sits on over nine acres of well treed, beautifully landscaped land in Ennis Bay, Lake Muskoka. Boasts 250' of prime Lake Muskoka frontage, a three-bedroom main cottage, one-bedroom guest cabin, two additional bunkies (each…

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