Starting at CA$1,950.00 a night
5000 sqft
This private island enclave features a modern lake house where no expense has been spared in ensuring luxury and convenience. Nap in a hammock on the private sandy beach, or carve a wave on a wakeboard - Cherry Island provides whatever experience you desire. Main floor master & guest room - both with ensuites. Living room with cathedral ceilings and wood burning fireplace bring a touch of class and comfort. Huge dining table seats 16+. The wall of windows allows for natural sunlight to stream in, giving fantastic views of the lake from all angles. Covered deck is the perfect spot to enjoy the outdoors if by chance it's raining. Upper level boasts an office area, complete with desk and comfy couch, with walk out to fabulous deck overlooking the water. Lower level houses four more bedrooms - three of them with ensuites. Up for a pool tournament? Pool table in lower level awaits! Flat screen tv, and lots of seating for those not participating in the pool tournament. Perhaps a game of charades?! Plenty of room for whatever you choose.
Come experience everything the world famous Muskoka Lakes region has to offer! Stay on a completely private island! This 6 bedroom, 6 bathroom, 5000 sq ft, modern, luxury Cottage is sure to make all your Muskoka dreams come true. 
This is a must see property!

From the last Friday in June through Labour Day Weekend we rent by the week or month. Spring & Fall Long weekends are a 3 day rental. Check in 4pm-7pm, check out at 10am.

Sleeping Configuration:
Bedroom 1 - King bed - sleeps 2
Bedroom 2 - King bed - sleeps 2
Bedroom 3 - King bed - sleeps 2
Bedroom 4 - Queen bed - sleeps 2
Bedroom 5 - Queen bed - sleeps 2
Bedroom 6 - Queen bed + Double bed - sleeps 4
Common areas: 2 sofa beds - sleeps 2

• Fully equipped gourmet kitchen
• 3 Fridges with freezer above ~ 2 in kitchen and 1 in lower level
• Stove • Oven
• Microwave
• Dishwasher
• Coffee Maker & filters
• Dishes, Pots, Pans, Cutlery
• Baking items - Blender, hand mixer, cookie sheets, muffin tins.
• Washing machine & Dryer
• Propane BBQ
• Wood Fireplace + wood
• Water Purification system plus Water Cooler
• Geothermal Heating and air conditioning
• Life Jackets - please bring any specific sizes for children & teens. (we do have some child & youth sizes, inquire for sizes)

You will have access to the whole Island and Mainland properties. In the Spring, Summer, and Fall you will have access to our luxury Bentley pontoon Boat with enough gas for the week. We can not guarantee the Bentley will not need repairs due to any accidents with other guests. 
On the beach are 2 canoes, 2 kayaks, 2 SUP boards plus floating toys, noodles and beach toys.

Golfing - Diamond in the Ruff & Windermere Golf clubs are less than 15 mins away.
Triathlon Training - amazing biking routes, swimming & challenging runs.
Swimming - in our crystal clean lake. our lake is usually quite a bit warmer than other lakes. it is deep but it is a smaller lake, which means warmer water :).
Beach Relaxing
Sand castle building
Hiking & beautiful walks.
Boating - with our Bentley pontoon
Cliff Jumping - off a cliff near the waterfall
Waterfall Swimming - At fish hatchery waterfall & Park
High Lake Waterfall - smaller waterfall
Skeleton Lake Bluffs - go for the day from Skeleton Lake Marina
Beaver Den / Dam Trek (Short or long)
High Lake Bluffs - Across the lake, with west views
Island Night Hike (Owner Recommended)
Fishing - Summer & Ice Fishing - Fry your catch on the outdoor stone fireplace!
Moonrise watching (from Stephan's landing)
Paddle Boarding
Hammocking on the cliff
Campfires & Marshmallowing
Sparkler Mayhem! - bring your own
Deer and Animal trekking
Bull Frog catching
Bird watching - Loons nest on the Island!
Yoga on the upper terrace!

Concierge services are available for all our rental properties to make your stay stress free! Catering, private chef services, daily maid service, water taxis, yoga on the dock, boat rentals, trampoline and water lily rentals, grocery, wine and beer stocking and we can even arrange to have cocktails waiting upon your arrival. Whatever you need just ask! We want to make your time at the cottage as relaxing and fun filled as possible!
King Size
King Size
King Size
Queen Size
Queen Size
Queen Size
Full Size

Onsite Services:

  • Concierge

Local Features:

  • Groceries
  • Hospital
  • Massage Therapist


  • Games for Kids
  • Satellite/Cable TV


  • Car Necessary


  • Bird Watching
  • Eco-tourism
  • Photography
  • Boating
  • Scenic Drives
  • Walking
  • Wildlife Viewing


  • Washing Machine
  • Wireless Internet
  • 2nd Refrigerator
  • Shampoo
  • Toilet Paper
  • Soaps
  • Filtered Water
  • Firewood
  • Laundry Soap
  • Linens
  • Paper Towels
  • Fireplace
  • Living Room
  • Washer
  • Carbon Monoxide Detector
  • Parking
  • First Aid Kit
  • Laptop Friendly
  • Safety Card
  • Essentials
  • Hangers
  • Smoke Detector
  • Internet
  • Towels
  • Hot Water
  • Private Entrance
  • Private Living Room
  • Extra pillows and blankets
  • BBQ Area
  • Bathtub
  • Air-Conditioning
  • Dryer
  • Central Heating
  • Hair Dryer

Location Types:

  • Lake Front
  • Village
  • Waterfront


  • Lawn / Garden
  • Wood Deck
  • Porch / Veranda
  • Terrace
  • Dock / Boatslip
  • Walkway to Water
  • Chairs
  • Firepit
  • Housekeeping
  • Patio Furniture
  • Kayak/Canoe
  • Deck/Patio

Kitchen & Dining:

  • Kitchen
  • Microwave
  • Dining Room
  • Dishwasher
  • Dining Area
  • Refrigerator
  • Oven
  • Cooking Utensils
  • Dishes & Utensils
  • Coffee Maker
  • Blender
  • Toaster
  • 4 Ring Stove


  • Adventure
  • Away From it All
  • Family
  • Historic
  • Luxury
  • Romantic
  • Sports/Activities

Attractions & Activities:

  • Kayaking
  • Swimming
  • Tubing
  • Lake



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House rules include:

All potential guests must complete a rental application where you will be asked to provide a full guest list, ages of all guests, the name address and employer of the primary applicant as well as their home insurance policy details. No reservation is confirmed until approved by the owner. The application will form the basis of your short-term lease agreement with the cottage owner and you understand and agree that you will abide by the terms therein. We will see you when you check in. If you have misrepresented yourself (your age, purpose of use) or your group, we reserve the right to cancel your stay without refund. If we find out after the fact you have automatically forfeited your damage deposit for breach of contract. We are looking for mature individuals who can be responsible for their actions, and show respect.
Rates are subject to change until your reservation is confirmed.
Linen, beach & bath towels included.
Pets are not permitted at this rental. 
No smoking, electronic or otherwise, inside the cottage.
Open fires in fire pit only please & check burn restrictions for area before you arrive.
Fireworks are NOT permitted.
Please leave the cottage as you found it, tidy and with all garbage disposed of per the welcome letter. Note there may be a garbage removal fee of $500 per week. The initial cleaning fee pays for professional cleaners to prepare the cottage for you. A check out clean may be arranged for an additional fee, otherwise you are expected to leave the cottage as you found it, tidy and in good repair.
WIFI is available at all of our cottages (unless specifically noted) but the service is not unlimited as this is cell based and extremely expensive. Streaming video services such as NetFlix, FaceBook, YouTube etc are not permitted, nor is online gaming. 5GB/ week is included. Overage will be billed at $10/GB.
Water activities, including motorized and non-motorized boating, are inherently dangerous. You indemnify the owners and their agents for any and all activities related to water activities.
To ensure the quiet enjoyment of the lake by our neighbours, music or loud noise of any kind not permitted after 10pm or before 8am.
Should you violate these terms you may be subject to an extra nuisance charge equal to the damage deposit as well as eviction without refund. 

**Check in times are between 4pm-7pm. Please ensure you arrive between these hours. Check out is 10am. Please have the pontoon at the main land landing by 10am as the cleaning team will be there at that time and will need the pontoon to get to the island.

Please leave the cottage as you found it and have a wonderful time at the lake!

Best regards,

The MDR Team

Fee Amount
Damage Deposit CA$5,000.00
Online Booking Fee 5%
Garbage Fee CA$500.00
Accidental Damage Waiver CA$125.00

Utterson , ON , Canada


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Stunning! Breathtaking!

Date of Stay:

Wow!! The property on Cherry Island is STUNNING, BREATHTAKING, a piece of HEAVEN! Spectacular views from every room in the house. Spacious, clean and plenty of indoor and outdoor activities for all to enjoy. It is the perfect place to unwind and rejuvenate. We made some great memories on this weekend getaway. Thank you again to Deena and Maryrose for being so kind, accommodating and bringing this weekend to fruition in such short notice.


Date of Stay:

“Incredible property”

Amazing! Incredible!

Date of Stay:

“Our weekend spent at this cottage was incredible. Amazing cottage, situated on a great island. Communication with Ross and his team was top notch. Thanks for a great weekend!!”

Beautiful, well cared for!

Date of Stay:

Beautiful house on high lake, taken well care of and friendly, quick responding host.

Excellent Excellent!!

Date of Stay:

This island is paradise! We were a big group and all the bedroom and en-suites, and seating areas, and patio furniture, and beach, and bar stools (ETC, ETC, ETC) made that place so great and livable. So grateful for Deena making it all happen. The space is spectacular and the customer service is just as good! All good things!

Can't wait to come back!!

Date of Stay:

Owner was extremely responsive, friendly, helpful, and accommodating. The property was simply amazing - Muskoka is one of my favorite places, and I had never experienced staying in a luxury home on an Island in High Lake, and it was incredible. The cottage was fully stocked with equipment, bedding, towels, soaps, shampoos, and it was clean. Can't wait to come back!

Amazing winter escape! Nothing compares!

Date of Stay:

I'm not even sure where to begin in reviewing Cherry Island. From the moment we stepped onto the frozen lake and made our way to the incredible island retreat, it was clear this was going to be a special weekend. We typically rent a ski chalet for our annual weekend escape of 15 friends, but this year decided to try something different. After this experience, we'll never be able to go back to a chalet! This place has everything you could want for a winter getaway - comfort, scenery, activities and fun! We raced down the sled luge, snowshoed to the waterfall, soaked in the hot tub and had fantastic meals gathered around the enormous dining room table. My deepest thanks to you for being exceptional hosts. If you'll have us, we'll be back in the summer and hopefully, for more winter weekends to come.

Ideal spot for a family reunion!

Date of Stay:

Amazing location and house! The listing actually undersells the property. The island is well built out with surprises throughout. Great spot for a party, event, family reunion etc. A+++++++++++++++++++++++++ (infinite)

Relaxed and lovely

Date of Stay:

Beautiful location. Great for a large group looking to relax and mess around on a quiet and lovely lake.

Perfection from start to finish!

Date of Stay:

We rented Cherry Island cottage for the Easter long weekend and everything was perfect! Very good hosts. Right from the beginning they were very helpful and welcoming. From towing our car from the icy road to helping our group carry our luggage and supplies for the weekend through the frozen lake with their snow mobile. They took the time to give us a tour of the cottage, answering our questions and explaining how specific kitchen worked. The cottage was very clean, the sheets freshly washed, the wood in the fireplace ready to be set on fire and the hot tub was running when we arrived. Our group had an amazing time and we would definitely recommend it to anyone who wants an unique Canadian experience. One thing to be aware of regarding the bathroom. If you are a big group, make sure that showers are not taken at the same time as there is a limited amount of warm water and the water heater takes some time to heat up. That being said, it was a great experience! Thank you!


Date of Stay:

Our group is so lucky to be able to stay in this stunning beautiful cottage. One must actually go into the cottage to feel how well build it is. Owner is a very nice and cool host also our group age is quite young. Overall we enjoyed the place very much and hope more people will have the chance to visit.

Would love to come back!

Date of Stay:

Fantastic Airbnb experience. We could not have asked for a more enjoyable weekend. A fantastic host, welcoming us into the home and even providing snowmobile transportation across the frozen like for all of our stuff. The cottage was outstanding. The cottage was exactly how I would imagine it from the description on the website. Our group would love to come back again and enjoy this amazing place.

The perfect cottage - has it all!

Date of Stay:

The cottage is everything that you expect and more. We spent our days boating around in the Bentley, canoeing and swimming in the lake (which was extremely warm). The host was very accommodating to the needs of our group and responded promptly to all of our questions during our stay. She made our check in and check out very easy. I would highly recommend this place!

Made phenomenal memories at this cottage!

Date of Stay:

We hosted our post-wedding party on Cherry island for 2 nights. What I can say is that it was an amazing and unforgettable experience, their hospitality and space made our wedding the best we could have asked for. Highly recommended.

Absolutely perfect!

Date of Stay:

We had a great stay at cherry island. Its a breathtaking location perfect for a getaway.


Date of Stay:

Best experience ever! Cozy, beautiful & luxury house with breathtaking views from every corners! 5-star amenities & services! We are a 4 family group had amazing 2 nights spent here, and definitely would return in the future. Thanks to the hosts for making our stay fabulous & impressive!


Date of Stay:

Thank you so much for making this weekend possible! We had an amazing time, everything was beyond perfect if that's even possible. We're stilll sharing photos and memories that will last a lifetime. This place is magical ***

Everything about it is fantastic!

Date of Stay:

Worth every penny. Hosts are fantastic and the cottage has all amenities. This was a memorable experience for everyone that attended.


Date of Stay:

Beautiful cottage on a perfect island!


Date of Stay:

The hosts made this a wonderful experience right from check-in. Great hosts; professional and down to earth. The property is gorgeous and would recommend to anyone. We had a blast.

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