Holiday rentals with lake access in Whitchurch-Stouffville

4.96 out of 5 average rating, 104 reviews

A dining table is set with decorative blue and white dishware. In the background, a fire pit is surrounded by red chairs, with vibrant greenery and a wooden swing adding to the outdoor ambiance. A flower arrangement and candles enhance the table setting.

Cottage in Innisfil

Greystone cottage in Innisfil

Welcome to our charming cottage in Innisfil, just a short walk from beautiful Lake Simcoe. Enjoy a spacious backyard featuring a cozy fire pit, a peaceful swing, bicycles and a BBQ area perfect for relaxing evening. You’ll find a fun game room equipped with AC, pool table, air hockey for entertainment during your stay. Conveniently located near grocery stores, Home Hardware, restaurants at Friday Harbour, and other local amenities. Come experience the beautiful atmosphere with your loved ones.

Cabin in Whitchurch-Stouffville

A charming cabin is nestled among tall evergreen trees, surrounded by well-maintained landscaping. Stone steps lead to the entrance, illuminated softly by exterior lights. The lush green lawn flows gently, creating a serene outdoor setting.

Lakefront getaway for two on Musselman's Lake

An amazing getaway space for two and your dog on beautiful Musselman's Lake, close to Toronto but feels like you're in the Muskokas. This rustic designer one-bedroom cabin is the original attached cottage that our house grew from. Sit at the dock or on your patio to watch the spectacular sunsets. Have a coffee in the backyard and watch the sunrise over 160 acres of trails out your back door. This is your retreat with high-speed internet, full-size kitchen & dining area to enjoy cottage life.

4.99 out of 5 average rating, 147 reviews

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, 106 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!

4.85 out of 5 average rating, 107 reviews

Home in Pickering

Luxury & Stylish 3BD | Chefs Kitchen & Cozy

Discover the charm of our inviting 3-bedroom house in the heart of Pickering's family friendly neighbourhood, West Shore. Featuring a newly renovated luxurious chef's kitchen, comfortable living space, and a tranquil layout, our home offers the perfect blend of relaxation and convenience. With Frenchman's Bay just minutes away, you'll have easy access to the best of the beautiful lake. Convenient Location - Minutes to Go Station, Pickering Town Centre and HWY 401! 25 Min. to UNION STN Via GO

4.98 out of 5 average rating, 567 reviews

A tree house is nestled among tall trees, featuring a wooden structure with a balcony and staircase. Soft sunlight filters through the branches, highlighting the natural wood finish and the serene forest surroundings.

Treehouse in Port Perry

Treehouse on private, isolated forest (300 acres)

You will feel like you're a thousand miles from Toronto. Your own private space with several ponds for swimming, gazebo, fire pits, running water, hot shower, mtn bike and hiking trails. With 300 acres at your door step, you can choose not to see another soul during your stay or venture to a nearby winery, restaurants, shopping, horse farms, golf courses or ski hills! We are just 1 hour from Toronto with easy access off the 407. We also have an amazing log cabin for rent on the same 300 acres.

4.96 out of 5 average rating, 145 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!

The exterior of the house displays a stone facade, framed by trees and greenery. A large deck extends from the structure, featuring outdoor seating and a BBQ setup. Nearby, a driveway accommodates several vehicles, with spacious lawn surrounding the property.

4.92 out of 5 average rating, 209 reviews

Pearl by Lake Simcoe - with sauna and steam room

Spacious and bright newly renovated house with access to the lake. This 2700 sqf house has a very functional and beautifully decorated living/dining area, 2 state of the art kitchens, 6 cosy bedrooms and 3 full washrooms. Huge 400 sqf deck with BBQ and heater comfortably fits a large company outside. Enjoy indoor sauna and steam room for deep relaxation. Free Wifi. Large entertainment room with Smart TV, XBox, Kinect and a foosball table provide plenty of activities inside the house.

4.91 out of 5 average rating, 209 reviews

Dome in Zephyr

Glass Dome - Sleep Under The Stars- Free Sundays

Discover this new, stunning 22ft Glass Geodesic Dome nestled in the heart of Uxbridge. Imagine waking up surrounded by 360-degree panoramic views of the natural landscape Please note... its FULL WEEKEND STAYS ONLY - BOOK FRIDAY AND SATURDAY-SUNDAY IS FREE. This allows guests to fully enjoy their Sunday without feeling rushed to check out at 11am. Enjoy all day Sunday with option of staying the evening. 8X12 BUNKIE NOW AVAIL. SLEEPS 4 ( 2 bunk beds) $100 flat fee

4.91 out of 5 average rating, 304 reviews

Lakefront | Private Dock, Sandy Beach & Hot Tub

Lake Simcoe waterfront cottage with a rare shallow sandy-bottom shoreline, private dock, and hot tub. Enjoy swimming, kayaking, paddleboarding, fishing, BBQs, fire pit evenings, and breathtaking sunsets. Perfect for family vacations, holiday getaways, and groups near Toronto, just minutes from Hwy 404. Features 6 bedrooms, 4 bathrooms, a fully equipped kitchen, and spacious indoor and outdoor areas. Private, peaceful, and ideal for year-round Lake Simcoe getaways.

Superhost

The exterior of the cottage displays a modern architectural design with large floor-to-ceiling windows, allowing for ample natural light. A spacious wooden deck surrounds the front, featuring lush greenery and vibrant flowers, creating an inviting atmosphere for relaxation.

Cottage in Innisfil

Crystal Beach Cottage & Spa

**New Boat Launch 2026 In front Of Property** Serene lakefront cottage with breathtaking views! This cottage fronts on the East side & faces West for a mesmerizing sunrise & sunset. A few steps to the lake for a dip in the lake, sun bathing, paddle boarding (4 paddle boards) or a stroll up Innisfil Beach Park for a walk. An outdoor fire pit, sauna and hot tub awaits you at to relax and loosen up those muscles & release tension. A wonderful experience awaits you!

4.87 out of 5 average rating, 373 reviews

4.98 out of 5 average rating, 125 reviews

A private deck is showcased, featuring two black chairs facing a serene lake view. Lush green trees and foliage surround the area, enhancing the peaceful atmosphere. The calm water reflects the blue sky, creating an inviting spot for relaxation.

Cottage in Caesarea

Lakeside Cottage Getaway South Shore Lake Scugog

WELCOME TO YOUR LAKESIDE GETWAY! This ALL SEASONS rustic, private lakefront cottage (south shore of Lake Scugog) has 2 bedrooms, 2 queen sized beds, large bright living/dining room, pullout couch, newly renovated kitchen and bathroom, private dock, indoor fireplace/outdoor fire pit and a loft space. Located approximately 1.5 hours from Toronto, this cottage is the perfect place for families and friends to escape the hustle and bustle, relax and unwind.