House holiday rentals in Cook's Bay

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Top-rated house rentals in Cook's Bay

Guests agree: These houses are highly rated for location, cleanliness and more.

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Top Guest favourite

Home in Georgina

5.0 out of 5 average rating, 28 reviews

Water’s Edge

Welcome to Water’s Edge – Lake Simcoe, a cozy charming cottage retreat with private lake access just steps away via your own dock and boathouse. Enjoy peaceful days swimming, sunbathing, fishing, or relaxing on the rooftop seating area with stunning lake views. Inside, you’ll find a fully equipped kitchen, comfortable beds, high-speed Wi-Fi, and outdoor spaces with a BBQ, firepit, and plenty of room to unwind and enjoy nature. Perfect for couples, families, or friends seeking lakeside relaxation

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Top Guest favourite

Two black Muskoka chairs are positioned on a wooden dock, facing a serene lake. The sky is filled with soft clouds, casting gentle reflections on the water's surface, creating a peaceful atmosphere for relaxation.

Home in Gilford

5.0 out of 5 average rating, 47 reviews

Blu Lake House | Waterfront May/June Special

Enjoy a peaceful two-story waterfront cottage with beach access. The perfect escape! Located an hour from Toronto. This cottage includes pedal boat, kayak, paddle board, inflatable rafts, volleyball net, basketball net, and swings facing lake view. Unwind with Netflix, or enjoy the game room, which includes a pool table, foosball, hockey, basketball, and Xbox 360. Local attractions such as the Gateway Casino, Cooks Bay Marina, Indy Go-Kart, Tanger Outlet, Local Eateries, Farmer Markets and more.

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Top Guest favourite

A lakeside luxury retreat features a spacious exterior with a large deck and expansive yard. Lush green grass is surrounded by trees, and several outdoor seating areas, including a dining set and Muskoka chairs, are visible. A wooden dock extends into the calm waters of Lake Simcoe.

Home in Georgina

4.98 out of 5 average rating, 40 reviews

Royal Beach Lake House & Spa w/ Hot Tub & Sauna

Royal Beach Lakehouse & Spa is your perfect experience of lakeside luxury! Sink your toes into the sand as you relax with your loved ones, our luxury retreat boasts panoramic views of Lake Simcoe! Wake up feeling refreshed after enjoying your private infrared sauna and fun water toys and activities. End your days with a spectacular sunset from your lakeside hot tub & firepit! Our chef's dream kitchen also awaits! This fully equipped lake house is sure to become your next vacation destination!

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Guest favourite

Home in Georgina

4.89 out of 5 average rating, 44 reviews

Sunset Harmony on Cook’s Bay

🌅 SUNSET HARMONY | Cook's Bay Waterfront Retreat One of the last chances to enjoy summer on beautiful Cook's Bay! Escape to our 4.88★ waterfront retreat for families and groups. 🏡 Main House + Private Studio (exclusive use) ✔ 4 bedrooms • 3 bathrooms • 2 kitchens ✔ NEW private dock with lake access & swimming steps ✔ Year-round hot tub & wood-fired sauna ✔ Kayaks, paddle boards & paddle boat ✔ Spacious pergola deck with west-facing sunsets Relax, reconnect, and create unforgettable memories.

LocationFamilyCleanliness

Top Guest favourite

A dining area features a wooden table surrounded by high-backed blue chairs. A large television is mounted on a feature wall, while crystal chandeliers hang from the ceiling. A pool table is visible in the background, enhancing the inviting atmosphere of the space.

Home in Barrie

4.96 out of 5 average rating, 108 reviews

Pool Table 10MinsToLakeSimcoe King Beds ProfDesign

Luxury! Pool Table! 75" Smart TV! Thoughtfully curated design! Unleash your inner chef in the gourmet kitchen with a gas stove, all your cooking & baking needs. Bask in the lofty 10' ceilings, and explore the vibrant neighbourhood with top-notch restaurants, shopping, golf courses, driving range, Hwy 400, serene lake and beach access, all within 5-10 mins. 25 Mins from Snow Valley & Horseshoe Valley Resort. Your luxurious escape awaits! 2 King Beds, 4 Queen Beds, 3 Single Pullout Mattresses!

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Top Guest favourite

The exterior of the villa showcases a well-maintained brick facade complemented by a red-tiled roof. Lush greenery surrounds the property, with vibrant orange flowers blooming along the front. A manicured lawn enhances the inviting atmosphere, offering a serene setting amidst the trees.

Home in Innisfil

4.98 out of 5 average rating, 273 reviews

Luxe Villa with Sauna and Hot Tub @ Lake Simcoe

Our boutique style property is 45 minutes from Toronto, in a prestigious neighborhood off Lake Simcoe, near Friday Harbour Resort (FHR). The Villa offers a year-round five star experience of a luxury lodge. Great private place for family getaways, corporate retreats, anniversary celebrations. Amazing location for outdoor activities including fishing, boating, hiking, biking, skiing, snowmobiling. Enjoy the freewheeling and pleasures of a place that was designed purely for you to indulge in.

LocationFamilyView

Top Guest favourite

A spacious living area is viewed, featuring a comfortable dark sectional sofa with plush cushions. A wooden coffee table sits nearby, with a green plant adding a touch of nature. The sleeping area includes a cozy bed and a window allowing natural light to illuminate the room.

Home in Coldwater

4.98 out of 5 average rating, 180 reviews

Luxury Guest House with Private Hot Tub and Trails

Equipped with a 4 person Hot Tub and 60 acres of Private Trails, you're sure to find tranquility in our unique Guest House. And if you're feeling more adventerous, there's lots to do in the area. From Tree Top Treking to Golfing, and Skiing in the winter of course, Oro-Medonte is truly a four season destination that is sure to capture your heart. We are pet friendly! We allow up to three pets total. It’s $50 per pet, we charge for 3 pets upfront. Rebates are issued accordingly.

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Superhost

Home in Georgina

4.69 out of 5 average rating, 64 reviews

Beautiful Waterfront Cottage with Pool&HomeTheater

🌲Lake Simcoe Getaway Escape to our rustic-chic Lake Simcoe retreat—perfect for families and friends! Enjoy a private swimming pool, sunny backyard with BBQ, cozy pool table, and a premium home theater for unforgettable movie nights. Just minutes from the lake, this farmhouse-style cottage blends relaxation and fun. Whether you're exploring scenic trails or relaxing by the pool, it's the perfect spot to unwind and create lasting memories. Book your getaway today! 🌞🌲

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Top Guest favourite

A cozy living area includes a navy blue sofa and a light armchair positioned on a patterned area rug. Decorative wall mirrors and plates are displayed above the seating. A lamp and a small table add to the brightness, while bar stools are positioned near the kitchen counter.

Home in Barrie

4.96 out of 5 average rating, 150 reviews

Bright basement apt with private entrance, Barrie

Welcome to Your Bright Basement Retreat in Barrie! Our cozy and modern 2-bedroom basement apartment offers the perfect balance of comfort and privacy. Located in a quiet residential neighborhood, it’s ideal for couples, small families, or business travelers. With its own private entrance, high-speed Wi-Fi, a fully equipped kitchen, and convenient access to downtown Barrie and the GO Station, this apartment has everything you need for a comfortable stay.

ValueFamilyDecor

Guest favourite

A comfortable bedroom features a spacious bed dressed in crisp white linens, complemented by dark decorative accents. Two lamps provide soft lighting on either side of the bed. A large window allows natural light to fill the room, framed with dark curtains.

Home in Barrie

4.94 out of 5 average rating, 340 reviews

Home in Barrie - Minutes to RVH & Georgian College

Minutes from RVH Hospital, Georgian College, Hwy 400, and the Barrie Waterfront. Clean, newly renovated, main floor of home in a quiet neighborhood. Your family will be close to everything when you stay at this centrally located place. Brand new tv in every room. Please inform us if you would like any extra linen or towels. Please note during WINTER months we can ONLY accommodate 2 cars. NO BACKYARD ACCESS .

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Top Guest favourite

An open-concept living room is highlighted by natural light pouring in through large arched windows. A comfortable white couch is paired with accents of black and brown. A decorative fireplace adds warmth, while modern furnishings create a welcoming atmosphere.

Home in Georgina

4.97 out of 5 average rating, 35 reviews

Lake Days & Cozy Nights – Your Year-Round Retreat

Cozy, family-friendly cottage just a short walk from the lake! Enjoy peaceful mornings on the porch, fun afternoons exploring nearby trails or public lake access, and evenings by the firepit. Perfect for families or friends, with a fully equipped kitchen, comfy spaces, and games for all ages. Relax, reconnect, and enjoy a quiet getaway surrounded by nature—where making memories is easy and the pace is slow.

FamilyLocationCheck-in

Top Guest favourite

An aerial view showcases the retreat's surroundings, featuring a landscape of lush greenery with a private lake in the background. The property, set in a residential area, includes several houses and a clear path leading to the water's edge, emphasizing the peaceful environment.

Home in Georgina

4.94 out of 5 average rating, 33 reviews

5 bdrm home with pool and private lakefront

Relax with the whole family at this peaceful retreat with a pool and private lake access just 7 minutes from the 404 and 45 minutes from Toronto. Enjoy breathtaking sunsets and swim safely in the sandy-bottomed lake, 3-6 feet deep within 150 meters of shore. Nestled in a quiet neighborhood yet close to supermarkets, restaurants, and LCBO, this retreat has everything for an unforgettable stay.

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