Holiday houses in Cumberland Beach

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Top-rated holiday rentals in Cumberland Beach

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Guest favourite
A spacious living area features a comfortable brown sofa positioned near a glass coffee table. Natural light pours in through large windows with blinds, illuminating a dining area with seating for four. A modern kitchen is visible in the background, equipped with sleek appliances.
Guest suite in Moonstone
4.86 out of 5 average rating, 291 reviews

RELAX @ our HOT TUB and SAUNA in the woods

PLEASE READ! Mt. St. Louis & Horseshoe Valley at doorstep! This is a bright, large and private walk-out GUEST SUITE (basement apartment). Hot tub, patio, fire pit & secluded path in the woods to enjoy nature. Kitchen is equipped with an induction cooktop and all things necessary, even wine bottle opener:) Open concept living room/kitchen/dining room with TV & Roku. Bedroom is a work of Art: dark, mysterious and romantic! Custom Queen bed made from weathered barn wood salvaged from our property.

Guest favourite
Cottage in Washago
4.87 out of 5 average rating, 137 reviews

Vintage Farmhouse Lakeview and Golfers Cottage

Perfect getaway 1.5 hours from Toronto. Custom vintage themed private cottage across from the lake and steps away from a 27 hole golf course. Nestled on private large wooded lot with room for your family to unwind. Spacious open concept living area with large fireplace. Vintage arcade games, foosball table, board games and yard games.. Two private deck areas for outdoor lounging/picnicking. Year round activities, kayaking, fishing, swimming (lake across road), golfing, skiing. Casino 18 min

Guest favourite
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
4.9 out of 5 average rating, 21 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!!

Superhost
A spacious living and dining area is presented, featuring a modern dining table set with plates and cutlery. A large sectional sofa faces a wall-mounted TV, with ample natural light filtering through sliding glass doors that open to a deck overlooking the outdoors.
Bungalow in Orillia
4.91 out of 5 average rating, 103 reviews

Charming Main Floor w Hot Tub

Welcome to our charming main floor apartment in the beautiful city of Orillia! This space is is suitable for families or small groups looking for a comfortable stay in a convenient location. This is a fully furnished home that features three bedrooms, one bathroom, a fully equipped kitchen with all the essentials needed to prepare your own meals. The living room is bright and cozy with a 43" Samsung Smart TV including Netflix, unlimited high speed internet and a spacious 6 seater dining table.

Top 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
4.99 out of 5 average rating, 151 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).

Superhost
The cozy living room features wooden walls and a gas stove. Natural light streams through large windows, illuminating a comfortable white sofa and a wooden coffee table. A textured rug lies beneath, complementing a minimalist aesthetic with a few decorative elements.
Cabin in Washago
4.92 out of 5 average rating, 269 reviews

Black River Haus - Scandi Riverfront Cabin Muskoka

Follow us on IG: @visitblackriverhaus The Black River Haus is a Scandi-inspired renovated 1970s cabin offering 3 beds + 1 bath and 140 ft riverfront near Muskoka, Ontario (20 min to Gravenhurst & Orillia). The cabin has been renovated and designed with the surrounding nature in mind, featuring a rustic living room & fireplace, fully-equipped kitchen and an outdoor patio & firepit. The Black River is 30 km long and is perfect for kayaking, canoeing and exploring.

Guest favourite
The cozy blue cabin is nestled among trees, showcasing a sloped roof and a vibrant yellow front door. Natural surroundings provide a serene backdrop, while a gravel path leads to the entrance, hinting at a peaceful retreat in the heart of nature.
Cabin in Hawkestone
4.84 out of 5 average rating, 116 reviews

Blue Dreams Of Lake Simcoe

Welcome to "Cabin Dreams Of Lake Simcoe" - your cozy blue cabin retreat in the heart of Hawkstone, Ontario, Canada. Immerse yourself in nature while enjoying modern comforts and nearby attractions. Our newly renovated 1 bedroom, 1 bathroom offers a unique getaway for couples, located just 1 1/2 hours outside of Toronto. **PLEASE NOTE** **Stairs leading up to the bed room loft are steep and may not be suitable for guests with mobility issues**

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, 263 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 a cottage is shown, surrounded by lush greenery and blooming flowers. A stone pathway leads to the entrance, with a wooden deck overlooking the lake. The tranquil water and open sky are visible in the background, accented by a large tree providing shade.
Cottage in Orillia
4.94 out of 5 average rating, 121 reviews

Spacious Cottage Escape with Lakeside Hot Tub

Escape from the usual! Bring your crew to our spacious 5 bdrm, 2 washroom, Lake Front cottage and RELAX. Enjoy the warmth of the fireplace and the beautiful view from the sunroom. Soak in the hot tub and watch the sunset. Proximity to Orillia's shops and restaurants. Casino Rama is 2km away for a completely different kind of fun. Two adult Kayaks available in spring and fall. Hot tub and bbq year round.

Top Guest favourite
An outdoor fire pit surrounded by gravel is present, featuring two wooden chairs. A hot tub is located nearby, positioned in front of a geodesic dome with large windows. String lights are draped overhead, illuminating the outdoor space.
Dome in Utopia
4.96 out of 5 average rating, 151 reviews

Glamping Dome Riverview Utopia

Come retreat into nature at the Riverview Glamping Dome… a 4 season getaway located on Rustic Roots Farm and Eco-retreat 1 hour north of Toronto. Whether you're looking for a romantic getaway or to come disconnect from the hustle and bustle of everyday life this geodesic dome is for you! Located on 64 sprawling acres come explore hiking trails, go fishing, relax in the hot tub, and stargaze fireside.

Top Guest favourite
A spacious living area features a modern kitchen with stainless steel appliances and light cabinetry. A comfortable sofa is paired with a low coffee table, adorned with greenery. Natural light flows in through large windows, enhancing the inviting space.
Apartment in Coldwater
4.96 out of 5 average rating, 114 reviews

Cozy getaway for two with hot tub!

Unwind in our peaceful guest suite attached to our home located near Mount St-Louis Moonstone, Vetta Nordic Spa and the cozy town of Coldwater. With its private entrance, hot tub (accessible daily between 8am and 10pm) and serene forest surroundings, this space is designed for guests who value calm, quiet and nature. We ask that guests share our appreciation for a tranquil environment.

Guest favourite
A spacious private room is visible, featuring a comfortable couch and a wooden coffee table on a soft area rug. A double bed is positioned along one wall, with natural light streaming in through patio doors that open to the outside deck.
Guesthouse in Washago
4.92 out of 5 average rating, 98 reviews

Waterfront Muskoka guest suite near Casino Rama

Take a break and unwind at this peaceful oasis surrounded by trees and wildlife in Washago, on the Black River. Conveniently located 10 minutes from Casino Rama, Hwy 11, groceries and a beach. Large private room with private entrance and bathroom overlooking the river with walkout to a deck and Muskoka chairs. Relax and recharge in nature in this quiet beautiful natural setting.

Popular amenities for Cumberland Beach holiday rentals

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