Holiday rentals in Cook&#x27;s Bay

Dome in Bradford West Gwillimbury

Vibrant autumn foliage displays shades of yellow and orange surrounding a geodesic dome. A pathway of stone steps leads through a lawn covered in colorful leaves, creating a serene outdoor setting amidst lush greenery.

Four season glamping dome under the stars

Whether you are looking for a romantic getaway for two, a solo remote work week in solitude surrounded by nature, or a family adventure, this 4-season geodesic dome is just the right place. Explore picturesque trails of Scanlon Creek Conservation Area, enjoy inground pool in summer, experience breathtaking sunsets over the farm fields, the starry skies by the bonfire, mesmerizing dance of fireflies in June, and let the frogs and crickets lull you to sleep in the place where time stands still...

4.97 out of 5 average rating, 499 reviews

5.0 out of 5 average rating, 32 reviews

Home in Georgina

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

5.0 out of 5 average rating, 49 reviews

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

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.

4.9 out of 5 average rating, 211 reviews

Waterfront Cottage-Sauna, Dock, 4-bed, 4 Parking

Bright and airy waterfront cottage in one of Lake Simcoe’s most desirable areas. The open-concept layout and unique lot design offer stunning lake views from almost every room. Enjoy custom furnishings, stylish decor, and a fully equipped kitchen—perfect for relaxing getaways or extended stays. Whether you're here for a peaceful retreat or lakeside fun, this cottage provides comfort, beauty, and convenience in a serene upscale setting. Ask us about fun activities that Lake Simcoe offers.

A covered patio area features a hot tub alongside a glass-topped table with comfortable seating. The peaceful lakeside view showcases expansive green space and a row of chairs positioned along the shore, framed by trees lining the property.

4.96 out of 5 average rating, 103 reviews

Sunset Shores Lakehouse- Hot Tub, Wet Bar & Games

Welcome to Sunset Shores Lakehouse! Nestled in a tranquil bay on the shores of Lake Simcoe, this spacious family lake house is the perfect escape in all 4 seasons with many indoor and outdoor activities to enjoy! This peaceful waterfront retreat boasts 4 bedrooms + Wet Bar + Patio Oasis with lakeside Fire Pit + 6 person Hot Tub overlooking the lake and spectacular daily sunsets and sunrises you wont want to miss! Only 1 hour from Toronto and close to many Georgina attractions and adventures!

4.94 out of 5 average rating, 88 reviews

Farm stay in Gilford

PrivatePretty Farmhouse, 1 HR to GTA,2 min 2 lake

Private 100 acres. Unique property, a very short distance from GTA (45 min), a short drive (10 min to Bradford GO station) this charming, private country farmhouse is close to beach area, hiking, bbq, biking, private trails, fishing opportunities...space for kids to play plus a campfire area to roast s'mores and enjoy the amazing sky. It’s a great place to relax, away from the city. Lots of deer to see on the property. Amazing for a working holiday or family visit. Steps away from Lake Simcoe.

4.85 out of 5 average rating, 85 reviews

The cottage presents a charming exterior, showcasing a white facade with decorative trim. A neatly paved driveway leads up to the entrance, framed by vibrant yellow flowers and lush greenery. A clear view of Lake Simcoe is visible in the background under a bright blue sky.

Home in Gilford

Beautiful lakefront Cottage on Lake Simcoe.

This private 3 bedroom cottage is a perfect getaway with family & friends. It offers a relaxing setting of lakefront view of Lake Simcoe year-round, a perfect place to unwind and relax on a hot summer day or bundled up to get out for some ice fishing fun. This cottage has a private waterfront and dock. A spacious living area features a gas fireplace, open kitchen and separate dining area. Equipped with an outdoor BBQ and a fire pit for roasting marshmallows under a starry night. Wi-fi ready.

4.86 out of 5 average rating, 267 reviews

Cottage in Innisfil

3BR on Lake Simcoe | Gorgeous Views 1hr From City

Escape the city and unwind at our peaceful three-bedroom lakefront cottage on Lake Simcoe, just one hour north of Toronto. With 129 feet of private waterfront, expansive lake views, and shallow swimmable shoreline, it’s the perfect year-round getaway for families, couples, or friends looking to relax and reconnect. 🌅 Stunning sunrise lake views 🏖️ 129 ft of private waterfront 🏊 Shallow, swimmable shoreline 🔥 Cozy all-season retreat 🌲 Quiet and peaceful setting 🚗 Just 1 hour from Toronto

4.9 out of 5 average rating, 49 reviews

Home in Georgina

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.

4.96 out of 5 average rating, 138 reviews

Resort-Style Luxury Waterfront Cottage

Experience luxury at our 5-star, Superhost-rated waterfront cottage on Lake Simcoe, just 80 KM from Toronto! A guest favorite, it offers breathtaking sunsets and sunrises from the living room and loft. Relax on the sandy beach with waist-deep waters, and enjoy the patio, BBQ, bar, lounge, kayaking, and fishing. With a fully equipped kitchen, 3 bedrooms, and 2 bathrooms, it comfortably accommodates up to 8 guests. Book your dream getaway today for the perfect blend of relaxation and adventure!

4.91 out of 5 average rating, 301 reviews

Lakefront | Hot Tub, Private Dock & Sandy Beach

Luxury lakefront cottage on Lake Simcoe with a rare shallow sandy-bottom shoreline, private dock, and hot tub—perfect for swimming and family fun. Enjoy breathtaking sunsets, kayaking, paddleboarding, fishing, BBQs, and a fire pit. Ideal for family vacations, holiday getaways, and group retreats near Toronto, minutes from Hwy 404. Features 6 bedrooms, 4 bathrooms, a fully equipped kitchen, and an open-concept living area. Private, peaceful, and perfect for unforgettable memories year-round.