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Holiday rentals in Cumberland Beach

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Top-rated holiday rentals in Cumberland Beach

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Top guest favourite
A tranquil lakeside dock is highlighted under a colorful sunset, with four chairs positioned for optimal viewing. The still water reflects the vibrant hues of the sky, creating a serene atmosphere. Lush greenery borders the scene, enhancing the natural beauty.
Cottage in Severn Bridge
4.99 out of 5 average rating, 205 reviews

CozyPeaceful LakeCottage HotTub Canada

Cozy Lakefront Cottage located on Sparrow Lake is the idea of relaxation. Enjoy the stunning sunsets while lounging on the large deck with a beverage in hand. The loons singing in the background. Perfect to enjoy with the whole family or on a couples retreat. The area is perfect for boating, fishing, walking, and biking around the neighbourhood. A mini toboggan hill Sparrow Lake is part of the Trent-Severn Waterway and you can boat to either Georgian Bay or Lake Couchiching in a few hours

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Cottage in Washago
4.86 out of 5 average rating, 140 reviews

Vintage Lakeview Cottage w/ Fireplace -Four-Season

Cozy four-season lakeview vintage cottage with a real stone fireplace—perfect for year-round stays. Just 1.5 hours from Toronto, directly across from Lake St. George and 30 minutes from Horseshoe Valley/Mt. St. Louis Ski Resorts. Enjoy swimming and kayaking in summer, and skiing, tubing, nearby trails, Nordic skiing and spa days in winter—stone fireplace, arcade games, foosball, firepit, BBQ deck & private wooded backyard. Minutes from Orillia and Casino Rama. 1GB Wi-Fi for remote work. Pets ok

Top guest favourite
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
4.96 out of 5 average rating, 156 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.

Guest favourite
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, 159 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).

Top guest favourite
An exterior view of a modern black tiny house is depicted, surrounded by trees and natural foliage. Two sets of stairs lead to the entrance, with a gravel pathway visible. Window placements create a unique design, and soft lighting illuminates the scene against the evening sky.
Home in Gravenhurst
4.98 out of 5 average rating, 211 reviews

Woodland Muskoka Tiny House

Enjoy the sounds of nature when you stay in this unique tiny house. This 600 sq ft home is nestled amongst 10 acres of towering trees, granite rock and trails to explore. The tiny home will not feel so tiny once inside. With high ceilings, plenty of windows, and surprisingly spacious rooms - it is the perfect hideaway for those wanting to unplug in Muskoka. The three season, screened in porch invites you to enjoy your coffee (or wine!) in nature without being bothered by the mosquitos!

Top guest favourite
A handcrafted timber frame cabin is set among trees, featuring natural wood siding and large windows that invite the outdoors in. A welcoming porch is accessed by a wooden staircase, while a covered area to the side provides shelter. The surrounding forest complements the rustic design.
Cabin in Bracebridge
5 out of 5 average rating, 254 reviews

Secluded Lakeside Retreat - Atkins Hideaway

Tucked in the heart of Muskoka, this handcrafted timber frame cabin rests alongside a scenic spring-fed lake, surrounded by 8 acres of private forest. Only 10 minutes from Bracebridge, enjoy serene lake life and natural beauty while remaining close to town amenities, local shops, and eateries. Enjoy private dock relaxation, cozy cabin comforts, and outdoor fires. A Provincial Park Day Pass is included (*security deposit required) for added adventure. Come relax, recharge and reconnect.

Top guest favourite
A spacious cottage is set against a lush green backdrop, featuring a distinct barrel sauna nearby. A manicured lawn hosts a small putting green with flags, alongside several lounge chairs. The architecture blends modern and natural elements, creating an inviting outdoor environment.
Cottage in Washago
4.96 out of 5 average rating, 118 reviews

Waterfront Cottage sauna/golf/kayaks/beach/games

Welcome to Hally’s Cove Riverside Retreat! A fully loaded 4-season escape on the Trent Severn River! Dock your boat with shore power ⚓, lounge in the over-the-water hammock 🌅, relax in the panoramic sauna 🧖‍♀️, or play in the games room 🕹️ (ping pong, basketball, air hockey plus lots more). Enjoy the 4-hole putting green ⛳, 6 kayaks 🛶, lily pad and custom landscaped Muskoka rock fire pit 🔥. Summer Bonus - Mosquito-sprayed for extra comfort! IG to see more photos: @hallys_cove

Top guest favourite
A spacious exterior view of the home is depicted, showcasing a well-maintained façade with multiple gables and a large driveway. Lush greenery surrounds the property, complemented by flower arrangements near the entrance.
Guest suite in Severn Bridge
4.97 out of 5 average rating, 128 reviews

Muskoka Retreat

Very spacious apartment (approximately 1600 sq. ft.) with private entrance. Located in Severn Bridge close to Hwy 11 at the Trent Severn waterway only 10 mins south of Gravenhurst. There are approximately 20 lakes and rivers within 30 minutes of the house with the closest one being only 5 minutes away. A guide book is offered in the suite that is full of recommendations for fun! Between Gravenhurst, Orillia, Bracebridge and Bala, there is always something exciting going on!

Guest favourite
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, 266 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!

Guest favourite
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, 134 reviews

FRIEND 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.

Top guest favourite
A cozy living area is presented, featuring a comfortable gray couch adorned with a blue throw pillow. A wooden coffee table holds a decorative tray with two books and a small potted plant. Natural light enters through a nearby door, framing a view of the lush greenery outside.
Guest house in Orillia
5 out of 5 average rating, 102 reviews

Forest Haven Guesthouse

Forest Haven Guesthouse is a scenic countryside property surrounded by trees and private trails. Your all-season, all inclusive getaway is just minutes from downtown Orillia. Your guesthouse which includes 3 bedrooms is a completely separate unit which is attached to our home. You have a keypad entrance and a front and back deck that are just for you! Happy travels!

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, 160 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.

Popular amenities for Cumberland Beach holiday rentals

  1. Airbnb
  2. Canada
  3. Ontario
  4. Simcoe County
  5. Cumberland Beach