Vacation rentals in Cumberland Beach

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Top-rated vacation rentals in Cumberland Beach

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Top guest favorite

Cottage in Menoke Beach

5.0 out of 5 average rating, 28 reviews

Bluewood Lake Cottage

Our 4 season family cottage on Lake Couchiching has been with us since 1951. It is newly reno'd top to bottom(July/25) and has 100ft of private lake front. Beautiful lake for swimming, fishing or boating and there is a boat launch 2 min away. We also have 4 kayaks and a peddle boat for you to use, but the crowd fave is our 18x6 blue floating swim mat! 5 mins up the road is the famous Webers, Starbucks and Tim Hortons. Just 1.5 hrs north of Toronto, 10 minutes north of Orillia in Menoke Beach.

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Guest favorite

A spacious living room features a comfortable sectional sofa arranged around a wooden coffee table. A large flat-screen television is mounted on the wall. Decorative plants and framed artwork enhance the cozy atmosphere, while ample natural light illuminates the space.

Home in Orillia

4.91 out of 5 average rating, 22 reviews

Upper Shadow Creek Haven - Waterfront

Escape to a newly renovated 1-bed, 1-bath cottage in Orillia, located off the canal leading to Lake Couchiching. Fully updated with a cozy living room, charming reading nook, and a deck with BBQ. Enjoy outdoor activities with boat docking, a private beach, and nearby park. Explore Casino Rama, public beaches, and downtown Orillia. In winter, access OFSC snowmobile trails, ice fishing, skating, and skiing. Whether seeking relaxation or adventure, this cottage offers a perfect year-round getaway!!

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Top guest favorite

A spacious hot tub overlooks the Severn River, surrounded by greenery. Chairs are positioned nearby on the grassy lawn, providing a relaxing space to enjoy the water views and sunshine. The calming river scene features boats gently cruising by, enhancing the outdoor experience.

Cottage in Severn Bridge

4.95 out of 5 average rating, 179 reviews

CARL in Muskoka: Waterfront Cottage with Hot Tub

Enjoy your own piece of Muskoka in this beautiful waterfront cottage! Only 90 minutes from Toronto nestled away on a private road along the Severn River sits CARL. Not a man... but a way of life. The Cottage and River Life! CARL is your retreat from the city, perfect for getting out in nature and experiencing everything life on the water has to offer. Whether you enjoy swimming, kayaking, great fishing or just relaxing on the dock or in the hot tub taking in the views... we've got you covered.

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Guest favorite

A cozy living area features two armchairs and a comfortable sofa, arranged around a central coffee table. Large windows allow natural light to illuminate the space, showcasing views of the surrounding woods. A television and a stylish lamp enhance the room's functionality.

Cottage in Washago

4.97 out of 5 average rating, 175 reviews

Relax at The Rock: Muskoka Waterfront Cottage

Enjoy fishing, swimming and paddling 22km of the green and black rivers. Paddleboat, canoe, 2 kayaks, and a SUP provided. Take the short 5 minute stroll into town for ice cream or fresh baked treats. Lay out on the elevated deck or in the screened in porch with a good book. End your evening at the riverfront firepit. Nearby day adventures include hiking, golfing, parks, beaches, breweries, casino rama, and downhill skiing at Mount St Louis Moonstone and Horseshoe Valley (30 minute drive).

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Guest favorite

A spacious two-story home, characterized by a stone façade and large front windows that offer a stunning view of the sunset. The well-maintained lawn is adorned with neatly trimmed shrubs and flowers, leading to a welcoming entryway. The outdoor seating arrangement is visible, suggesting an inviting area for relaxation.

Cottage in Orillia

4.92 out of 5 average rating, 48 reviews

Lakefront Simcoe Cottage | Dock&Kayaks |Firepit

Escape to the shores of Lake Simcoe for a relaxing four-season getaway with family and friends. This 4-bedroom lakefront cottage sleeps up to 8 guests and offers beautiful water views, direct lake access, fishing, kayaks, a canoe, paddle board, and fire pit. Start your day with peaceful mornings by the water, spend the afternoon fishing , kayaking, paddling, or swimming in season, and unwind by the lake . Just a short drive from Downtown Orillia, Casino Rama, and year-round attractions. 😊

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Guest favorite

A stone pathway leads to a fire pit surrounded by colorful Adirondack chairs in red and yellow. The view overlooks the lake, with a dock extending into the water under a clear blue sky, providing a serene setting for gatherings.

Home in Orillia

4.82 out of 5 average rating, 318 reviews

Waterfront Cottage Over-the-Water view w BBQ& Wifi

Our cottage backs directly onto lake Simcoe with a view overlooking the water reminiscent of a four season water villa bungalow. Enjoy the entire house with your family and friends and be captivated by nature's beauty as the sun sets behind the treeline across the lake. Easy access to lake Couchiching for fishing in the summer and ice fishing in the winter, 30 mins to Mount St. Louis for skiing and snowboarding, 30 mins to Vetta Nordic Spa and Casino Rama is only a 10 minute drive away!

LocationFamilyShared spaces

Luxe

The exterior of the cottage is showcased amidst tall trees, featuring large windows that create a bright and airy appearance. Soft lighting highlights the architectural details, while the serene natural surroundings provide a tranquil setting.

Cottage in Gravenhurst

4.99 out of 5 average rating, 87 reviews

Muskoka Lakefront• Sauna • Fireplace• Chef kitchen

Welcome to Edgewater Cottage Muskoka, a brand-new luxury retreat on a private bay, less than two hours from Toronto & 10 minutes from Gravenhurst, with great restaurants, scenic hikes, golf, and amenities. Perfect for families, friends, couples, groups, retreats, or small corporate off sites. When booking please share a few details about your group. The property is for peaceful getaways and not available for parties. A signed rental agreement is required to confirm your reservation.

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Superhost

An indoor pool is framed by large windows that allow natural light to fill the space. The ceiling features wooden beams that create an airy atmosphere. Two chairs are positioned nearby, and vibrant yellow flowers are visible through an adjacent window.

Home in Orillia

4.77 out of 5 average rating, 105 reviews

Casa ~ Pool ~ Fire Pit ~ BBQ

Relax with the whole family at our peaceful forest estate. Mother nature is your only neighbour and she comes right to your doorstep to welcome you. Enjoy the peaceful serenity of the forest that surrounds you. Enjoy our pool, nearby ATV trails, and all the activities Orillia has to offer. Guest access You'll have access to the entire property. The backyard is completely private, with zero light pollution, so please enjoy the stars and the peace and calm of nature.

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Guest favorite

A bungalow with a wooden deck overlooks a well-maintained lawn, surrounded by greenery and flower beds. Large windows provide views of the outdoor space. The exterior showcases a warm wooden finish and a sloped roof, enhancing the inviting appeal of the home.

Bungalow in Orillia

4.87 out of 5 average rating, 277 reviews

Luxury, Waterfront, 4 bdrm Bungalow in Sth Muskoka

Just 1 kilometer past Webers on Hwy 11! A cozy home on the lake with all the amenities. This 4 bdrm 2 bathroom yr round bungalow sleeps 8 comfortably and is perfect for all seasons. Amenities include 2 full bathrooms, 2 full TV rooms, (1 with a double sectional) and a games room w/ Foozball. Outdoor person? Lots of Swimming, Fishing, Paddle Boat, Canoe, Reading, or a glass of wine by the water. Also just 15 mins from Casino Rama!

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Top guest favorite

Cottage in Severn Bridge

5.0 out of 5 average rating, 18 reviews

Waterfront Muskoka Cottage - Sauna & Kayaks

Escape to your own Muskoka waterfront retreat on the Trent–Severn Waterway. Swim from the dock, explore the water with 4 complimentary kayaks, unwind in the private outdoor sauna overlooking the river, then end the night around the fire pit. Sleeping up to 9 guests, Casa Duarte del Río is ideal for families, couples and friends looking for a peaceful four-season cottage getaway just a short drive from Gravenhurst.

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Top guest favorite

An open-concept living area features a comfortable light-colored sofa adorned with patterned throw pillows. A wooden coffee table sits in the foreground, while a dining area with dark wood chairs is visible in the background, complemented by modern kitchen cabinetry and stainless steel appliances.

Home in Severn

5.0 out of 5 average rating, 23 reviews

Spacious 4 Bedroom Retreat By Lake Couchiching

Welcome to our newly constructed, spacious 4 bedroom, 3.5 bathroom house in Severn, Ontario! Just a short walk from Lake Couchiching, with plenty of parks, trails, activities for all ages in the forest or water. Also a short drive to Casino Rama, Bass Lake Provincial Park, Couchiching Beach and the City of Orillia. With plenty of room and amenities, this place is perfect for a relaxing family or group getaway!

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Superhost

The exterior of the Lake House is surrounded by lush trees, with a wide wooden dock extending into the calm waters. A patio area features multiple red Muskoka chairs, inviting relaxation by the water's edge. Soft evening light hints at the cozy ambiance of the home.

Cottage in Orillia

4.86 out of 5 average rating, 149 reviews

AMIGO LAKE HOUSE

Amigo Lake House, the perfect getaway for any season! Sunny South waterfront views, soak up the sun during the day and star gaze the picturesque sky over the lake at night. Start the morning with a cup of coffee and watch the sunrise over the lake, explore on the kayak/paddle boards, play games in the backyard, barbecue a savoury meal, stay warm by the fire or take dip in the hot tub.

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