Cottage holiday rentals in Cherry Island

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Top-rated cottage rentals in Cherry Island

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Top guest favourite

A newly built blue cottage is surrounded by tall pine trees, featuring a large deck with outdoor seating. A stone pathway leads up to the entrance, bordered by rocks and flowering plants. The sloped landscape creates a natural and inviting approach to the home's exterior.

Cottage in Torrance

Lakefront Cottage Muskoka- Barclochan Lookout

Visit the heart of Lake Muskoka in this newly built 3 bedroom family friendly year round cottage. Located on Walker's Point on Lake Muskoka, you are within an easy driving distance of Gravenhurst, Bala, Port Carling and Bracebridge. Enjoy the scenic 2 level view from the living and dining room and kitchen on the main level, and the spectacular view from the loft and Primary bedroom with huge windows upstairs. Not suitable for party weekends. Primary renter must be a minimum of 25 years of age

5.0 out of 5 average rating, 107 reviews

Top guest favourite

A charming cottage is nestled among mature trees, showcasing a mix of modern and antique design elements. The exterior features a metal roof and wooden accents, with a welcoming staircase leading to the entrance. Large windows provide views of the surrounding natural landscape.

Cottage in Huntsville

The Rock Lodge, At Mary Lake (+ Hot Tub)

A charming little “Old meets New”cottage in the heart of Port Sydney, Muskoka. less than 5 min walk away from Mary Lake where you can enjoy the beach, have a picnic or even Launch your Water vessels into the lake for a relaxing day. Across the beach you can find a community centre with a play ground and basket ball court perfect for our younger guests. 2 km away from North granite ridge Golf Club; Our area is surrounded by preserved woodlands perfect for scenic hikes and spotting wildlife! ✨

4.99 out of 5 average rating, 322 reviews

Top guest favourite

Cottage in Utterson

6BR, Hot Tub, Lakefront - Muskoka Sunset Retreat

Private lakefront on quiet Three Mile Lake with west-facing sunsets, an 80-ft dock, and hot tub overlooking the lake—your classic Muskoka experience. Unwind by the firepit, paddle the lake, or relax on the deck at sunset. Inside, enjoy a fully updated cottage with spacious kitchen, fireplace, and panoramic lake views—ideal for group stays. Wake to the sound of loons, spend the day on the water, and settle in for evenings by the fire. Welcome to Shea on the Bay. License No: STRA-TML-25-00

4.96 out of 5 average rating, 104 reviews

Guest favourite

A sunlit living space features large windows with views of the lake, allowing natural light to fill the room. A cozy striped armchair and a simple wooden coffee table are positioned on a wooden floor. A round table with decorative placemats complements the inviting atmosphere.

Cottage in Parry Sound

Muskoka Waterfront w/ Hot tub (Silver Linings)

*No extra fees* Come enjoy our designer furnished, newly-built, 4-season, Silver Lining Muskoka Lakehouse. This cottage offers you and your loved ones the perfect getaway with tons to do and memories to make with Insta sunsets over a lake wrapping around the entire property, a sandy beach to dip your toes, hot tub to warm up with friends, fire pit for roasting marshmallows. Other amenities: fully stocked kitchen, treehouse, games, BBQ, 1 acre of privacy, pet bed, well maintained hot tub.

4.93 out of 5 average rating, 194 reviews

Top guest favourite

A modern cottage is set against a backdrop of tall trees, featuring a large wraparound deck illuminated by warm lights. A fire pit sits on a granite outcrop, surrounded by outdoor chairs. The peaceful evening sky casts a calm ambiance over the scene.

Cottage in Bracebridge

Tiny Luxury Cottage with Hot Tub

This tiny luxury 2 bedroom cottage 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, 186 reviews

Top guest favourite

Cottage in Huntsville

Escape to Falconview, Huntsville-Muskoka

Enjoy a piece of Muskoka in this beautiful waterfront cottage! This six bedroom home is only minutes away from historic downtown Huntsville, as well as many grocery stores and restaurants! Located on the Vernon Narrows, close to the mouth of Lake Vernon-Also, with boat access to Lakes Mary, Fairy and Peninsula, and a boat launch only a short ride away, it’s sure to impress! If you’re looking for a place to explore or just a spot to sit back and relax, we’ve got you covered!

4.99 out of 5 average rating, 147 reviews

Top guest favourite

A wooden dock extends over calm waters, featuring four Adirondack chairs in red and yellow. The serene lake reflects the surrounding trees and sky, with a light morning mist gently hovering above the water's surface.

Cottage in Port Carling

Gorgeous Muskoka Getaway on stunning private lake

Enjoy the perfect cozy Muskoka cottage "The Perch" on a beautiful private lake. This family and pet-friendly home is your year-round retreat. Your family will be close to everything when you stay at this centrally located place but you will feel like you are at a peaceful cottage surrounded by nature. With all of the amenities that you would need, you will find that The Perch is everything you are looking for to create memories with friends, families or a loved ones.

4.99 out of 5 average rating, 158 reviews

Top guest favourite

An inviting outdoor space features a hot tub and a unique sauna, surrounded by neatly arranged stone pathways. The backyard includes Muskoka chairs around a firepit, with lush greenery and trees creating a natural backdrop. A covered patio area extends the living space outdoors.

Cottage in Huntsville

Muskoka Spa & Golf Retreat with Sauna + Hot Tub

Embark on a family wellness journey at our Nordic farmhouse-style Cottage in Muskoka. Unwind in the wisteria-adorned hot tub or by the firepit, nestled in Muskoka chairs. This bungalow features airy ceilings, expansive windows, and a modern fireplace. While the en-suite offers a rejuvenating frameless shower and deep tub. The Muskoka river is 250m away, Port Sydney Beach a 10-min drive. Embrace year-round family fun and wellness. Your rejuvenating escape begins here.

5.0 out of 5 average rating, 184 reviews

Top guest favourite

A spacious outdoor deck is surrounded by trees, featuring a red umbrella over a seating area. A BBQ grill is positioned on the side, while flower pots add a touch of greenery. Lounge chairs invite relaxation in this tranquil setting.

Cottage in Windermere

Dragonfly - Muskoka - High Lake

A hidden gem on High Lake, this private two-bedroom cottage is where Muskoka whispers its secrets. Just 2.5 hours north of Toronto, tucked between Hunstville and Bracebridge. Built in a charming mini-Viceroy style, the cottage welcomes you with vaulted ceilings and warm, sunlit spaces. A cozy Muskoka room extends off to the side, inviting you to linger over long dinners or curl up with a book while the lake breeze drifts through.

4.94 out of 5 average rating, 146 reviews

Guest favourite

Cottage in Bracebridge

The Hudson - Riverside Cabin, Bracebridge

Tucked along the Muskoka River and thoughtfully reimagined, The Hudson is a moody, design-forward escape that blends classic Muskoka charm with timeless Ralph Lauren–inspired style. Rich wood tones, layered textures, and curated details create a cozy yet elevated atmosphere—perfect for couples looking to unwind in a space that feels both refined and relaxed. For more photos and information visit us thehudson.riversidecabin

4.91 out of 5 average rating, 379 reviews

Top guest favourite

A cozy living area features a sleek Norwegian gas fireplace, modern furniture, and large windows allowing natural light to fill the space. A wood beam ceiling enhances the room's height, while a vibrant piece of artwork adds a pop of color to the wall.

Cottage in Baysville

Dock | Modern Muskoka Waterfront

Enjoy the picture-perfect sights of Muskoka only two hours from downtown Toronto. Kayak on the Muskoka river, enjoy dinner on the oversized back deck, watch sunsets & stars, and roast marshmallows by the fire. This stunning two bedroom cottage is equipped with a fully modern interior. Keep warm by the beautiful Norwegian gas fireplace in the winter; stay cool with refreshing AC in the warmer months. DOCK has it all.

4.93 out of 5 average rating, 334 reviews

Top guest favourite

A wooden deck overlooks Brandy Lake, featuring a circular table surrounded by five red chairs. A dog stands on the deck, while a wooden dock extends into the calm water. Nearby, bright kayaks rest on the rocky shore, framed by natural foliage.

Cottage in Port Carling

Cider Haus | Lakefront Sauna & Fenced Yard

Welcome to Cider Haus, a quaint four-season Muskoka cottage on Brandy Lake, just five minutes from Port Carling. Spend summer days swimming and paddling, unwind in the lake-view sauna, and gather around the natural-stone fireplace when the weather turns cool. With a fully fenced yard, equipped kitchen, and thoughtful comforts throughout, it's a welcoming lakefront retreat for couples, friends, families and pets.

4.95 out of 5 average rating, 197 reviews