Holiday rentals in Cumberland Beach

4.87 out of 5 average rating, 15 reviews

Home in Orillia

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!!

4.96 out of 5 average rating, 127 reviews

Cottage in Severn Bridge

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.

4.74 out of 5 average rating, 85 reviews

Home in Orillia

Teddy Bear Cottage

Teddy Bear Cottage Gorgeous 4 bedroom 2.5 bathrooms, one with a jacuzzi is located in Cumberland Beach a small village in between Orillia and Gravenhurst near Washago and Webbers is just around the corner, peaceful beach with dock, quiet picturesque view with hot tub and lots of stars at night, only 10 mins to Costco, Walmart as well 30 mins to Mount St’louis, Also Hardwood Hills 20 minutes for those bikers and hikers.Outdoor camera backyard corner, 2front camera near door and garage(blink)

5 out of 5 average rating, 126 reviews

Cottage in Washago

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).

4.88 out of 5 average rating, 128 reviews

Cottage in Washago

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 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.

4.99 out of 5 average rating, 152 reviews

Holiday home in Orillia

Days Away! free parking - no cleaning fee

Welcome to Days Away! Hosted by Lisa and Brad Day. Our city and surrounding areas have so many events, attractions and seasonal activities. We love to explore so we know all the wonderful hidden gems. It is a central/convenient location. We entered hosting because we love to entertain and participate in local events/activities. Whether you are here for sports, attractions, festivals... We want to share this amazing area with you. Come stay with us and let us exceed your expectations!

5 out of 5 average rating, 182 reviews

Cabin in Bracebridge

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.

4.97 out of 5 average rating, 139 reviews

Flat in Orillia

Luxury 1 Bedroom Apt In The *HEART* Of Orilla

This Incredible unit is the perfect blend of style, luxury & convenience. Filled With all the amenities you look for with the touch of luxury that you would expect in a hotel. Spend your evenings relaxing with a glass of wine on the covered front porch, immersing yourself in the cinematic feel of the 75" TV, or walking through the bustling downtown streets of Orillia on the way to catch the sunset at the waterfront. However you choose to spend your stay, there is much to enjoy! 🤩

4.76 out of 5 average rating, 178 reviews

Cabin in Severn Bridge

Moon River Place Unit 4A

A modest riverfront cottage with a full kitchen and bathroom, three bedrooms that sleeps six; 1 queen, 1 double and a bunk. 20 mins from Orillia, and 15 mins from Gravenhurst. Situated on a lively canal connecting Sparrow lake and lake Couchiching with private access. Perfect for families or small groups looking to enjoy some time away from the noise of the city. Please read the listing details, if you miss important information, please do not make a complaint about it later.

Guest suite in Severn Bridge

4.96 out of 5 average rating, 107 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!

4.78 out of 5 average rating, 199 reviews

Cabin in Washago

Golfers' Paradise *Hot Tub and Kayaks

Authentic 3rd generation Canadian cottage (540sqft) just 90 mins north of Toronto. Wood stove, small quiet lake (access 2 min walk) large private lot. HOT TUB, firepit & kayaks. GOLFERS PARADISE! Walk to 9, 27 & mini courses & a great licensed restaurant (live entertainment). Close to Washago, Orillia & Casino. Pet friendly! Easy access to hwy; you will hear some hwy. noise. Free Muskoka Mosquitoes. 1-2pm check-in. Bring sheets, towels, firewood & drinking water.

4.87 out of 5 average rating, 248 reviews

Bungalow in Orillia

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!

Holiday rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodation and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Cumberland Beach holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Cumberland Beach

4.93 out of 5 average rating, 28 reviews

Home in Orillia

New Build Luxury - Family Cozy Orillia Home

CherieRating, 5 stars3 weeks ago

Beautiful house and very clean. Host was flexible and always quick to respond. Lots of restaurants and things to do close by. Very happy with our stay.

4.99 out of 5 average rating, 86 reviews

Home in Georgian Bay

A-Frame in the Woods of GeorgianBay, Muskoka

BecciRating, 5 stars2 weeks ago

We had a wonderful time celebrating our friend’s bachelorette. We’ll definitely have to come back one day when it’s a little warmer!

5 out of 5 average rating, 27 reviews

Guest house in Orillia

Woods Bay Cottage Severn

RuthRating, 5 stars1 day ago

Lovely quiet location, easy to get to. Thank you for looking after us so well. Enjoyed bikes and basketball !

Home in Severn

4.6 out of 5 average rating, 5 reviews

Severn Manor: 5B/3.5B – Custom Luxury & Comfort!

SarahRating, 5 stars2 months ago

Great area, beautiful place, would definitely visit again!

4.96 out of 5 average rating, 96 reviews

Cottage in Orillia

Shallow Shore Cottage

PamRating, 5 stars9 months ago

Great and peaceful place to stay! Neighbors are nice, scarce and quiet! Very private. Not totally remote but quiet except for a little highway noise during the day. Can’t hear it inside the house. Enjoyed relaxing by the water, on the porch, which was screened windows so when the weather is nice, the breeze from the lake felt awesome. My only complaint is the walls were a little thin between bedrooms. Beds are comfortable and kitchen was nice to cook in. Felt spacious and the fire pit was very nice. Highly recommend! And host was very responsive and friendly

5 out of 5 average rating, 13 reviews

Home in Severn

Luxury 3BR Villa w/ 2.5 Baths & Glowing Backyard

RaisaRating, 5 stars1 day ago

We really enjoyed our stay! The space was clean, cozy, and had everything we needed. Farida was kind and easy to communicate with. They made us feel welcome and were quick to help if we had any questions. Would definitely recommend this place to anyone visiting the area. Thanks again for hosting us!

4.99 out of 5 average rating, 165 reviews

Guest suite in Washago

Spacious Apartment Facing The Severn River

ElizabethRating, 5 stars2 weeks ago

Ed’s place is cozy, peaceful, and had everything we needed for the perfect long weekend getaway by the river/lake. Every space we used and spent time at, both indoors and outdoors (yard, patio, dock), was beautiful, clean, and spotless. The kitchen is nice and big, and there was lots of space for cooking and relaxing in the evening. The outdoor areas were super well-maintained. Amenities were also 10/10! We enjoyed hanging out on the dock, kayaking, fishing, and even learning how to bbq a steak for the first time on the grill! ☺️ Wish we had more time at the cottage to make a bonfire, maybe next time! Ed was an amazing host. He went out of his way to make sure we felt at home and was very responsive to all inquiries and requests. Thank you so much, Ed.