Holiday houses in Cumberland Beach

4.84 out of 5 average rating, 249 reviews

Guest suite in Moonstone

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.

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, 120 reviews

Cottage in Bracebridge

Tiny Luxury Cottage with Hot Tub

This tiny luxury 2 bedroom cottage with loft is perfect for a romantic couple or small family getaway. Nestled on 1.5 acres among majestic trees and granite outcrops, creates beautiful views from the deck with BBQ, fire pit, hot tub or massive windows throughout the cottage. Water dam and river across the road create relaxing waterfall sounds that are heard from deck or enjoy it close up from the private shoreline deck and dock. Explore the Muskoka River on the kayak, SUP or river tubes.

4.99 out of 5 average rating, 154 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!

4.97 out of 5 average rating, 139 reviews

Apartment 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, 179 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.

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Other great holiday rentals in Cumberland Beach

4.93 out of 5 average rating, 29 reviews

Home in Orillia

New Build Luxury - Family Cozy Orillia Home

SharonRating, 5 stars2 days ago

The only issue was the kettle was t clean and the pots and pans could be updated and other than that beautiful spot and area and wasn’t far from where we wanted to be .

5 out of 5 average rating, 27 reviews

Guesthouse in Orillia

Woods Bay Cottage Severn

RuthRating, 5 stars4 days 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!

5 out of 5 average rating, 14 reviews

Home in Severn

Luxury 3BR Villa w/ 2.5 Baths & Glowing Backyard

RaisaRating, 5 stars4 days 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.

4.82 out of 5 average rating, 28 reviews

Cottage in Washago

SouthLake Cottage on The Lake.

DonaldRating, 5 stars8 months ago

This listing is exactly as pictured. It is truly beautiful to look out over the lake at sunset (anytime, really, haha) and was the perfect location for some time away from the city. I was able to get to the listing from Toronto without a car as well, so good to know for accessibility from the city for anyone without access to a car. Overall, my experience at this listing was great. Saeid communicated with me very well--quick, informative, and efficient exchanges. He was helpful as much as possible and readily admitted when unsure of things. The kitchen covered all basic needs for cooking and serving food; the grill was nice to use as well. The jetted tub was unavailable during my stay, but that is a very minor detail in the context of a great stay at Saeid's place. I would definitely return and highly recommend.

5 out of 5 average rating, 12 reviews

Cabin in Tiny

The Beach House, Georgian Bay, Beach View w/ Sauna

SamRating, 5 stars4 days ago

My family and I had a great time at Adam’s cottage! Incredible view of the lake, the lake water was crystal-clear. Beach house was well maintained and very clean, the interior decor was stunning! Beach house/garage had all the amenities you will need! The 2 paddle boards and 2 bikes were a great edition! we enjoyed walks/bike rides through the trails in the neighbourhood. We will definitely come back, HIGHLY recommend! Adam was very helpful, insightful, and gave fast replies! Great host!