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Cottage holiday rentals in Cherry Island

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Top-rated cottage rentals in Cherry Island

Guests agree: These cottages are highly rated for location, cleanliness and more.

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Guest favourite
A rustic log cabin is nestled among tall trees, showcasing a welcoming entrance with a wooden porch. The surrounding foliage features various shades of green, while a canoe and kayak are positioned on the side, hinting at nearby water activities.
Cottage in Seguin
4.76 out of 5 average rating, 154 reviews

Muskoka Clearwater Log Cabin & Sauna

Nestled on the tranquil Clear Lake system just north of Lake Joseph, this Muskoka Log Cabin, built in 1938 by RW Wilson, offers an extraordinary retreat. This rustic, southern-facing cabin features crystal-clear waters, historic tall pines, a wood-fired sauna, and a private dock for a rare & captivating experience. The cabin uniquely showcases heritage log construction and the rich recreational history of the Georgian Bay region. Security cameras monitor the parking area 24/7 for your safety.

Guest favourite
A lakeside cottage is surrounded by tall trees, with a gentle slope leading to the water. A private dock is visible, along with several outdoor chairs. The cottage's warm glow is highlighted in the evening light, offering a welcoming appearance.
Cottage in Gravenhurst
4.88 out of 5 average rating, 178 reviews

Waterfront 3 BR Cottage 4 Seasons Gravenhurst Heat

4 Seasons: Heated+A|C! You and friends/family will enjoy easy access to everything Gravenhurst has to offer from our centrally located retreat cottage. Conveniently located on Pine Lake, you will have sun-filled water views throughout the cottage. We are located directly off the main highway, easy road access and parking. The lake is perfect for swimming and water sports. Get ready to sip your morning coffee on the back porch and watch the sun rise! A perfect spot for yoga and/or meditation.

Top Guest favourite
A wooden dock extends over calm waters, featuring two lounge chairs with blue and green stripes. The surrounding trees provide a lush green backdrop, while a cabin is nestled among them, visible on the hillside. A canoe rests on the shore, completing the serene lakeside scene.
Cottage in Huntsville
5 out of 5 average rating, 147 reviews

Muskoka Lake Hideaway +HOT TUB/Waterfront/Bonfires

*SUMMER AVAILS* Welcome to Muskoka Lake Hideaway. Enjoy a swim off the waterfront dock & dinner from the balcony to beautiful lake views. Follow with a soak in the gazebo-covered hot tub (rain or shine), marshmallows on the bonfire & nest away with classic board games. A boutique, 4-season cottage, perfect for a couples getaway or small family/friends vacation. For outdoor excursions, explore Arrowhead, Limberlost & visit Huntsville for restaurants, breweries & local amenities, minutes away.

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
4.99 out of 5 average rating, 302 reviews

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! ✨

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
4.99 out of 5 average rating, 169 reviews

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.

Guest favourite
The cottage is displayed under a starry sky, with warm lights glowing from large windows. A spacious deck extends from the cottage, complemented by lawn space. A small shed is visible to the side, set among trees that line the property.
Cottage in Huntsville
4.84 out of 5 average rating, 133 reviews

Beautiful Lake House

Welcome to our beautiful 4 season lakefront cottage that is close to the amenities of the towns of Bracebridge and Huntsville. Located on a quiet, private road 2 hours from Toronto, surrounded by nature. This beautifully renovated 4-bedroom, 2 full bath cottage has everything you need for a relaxing city escape! In the winter months, enjoy skating, hiking, skiing at Hidden Valley and a variety of winter activities at Arrowhead Park. Come back and sit by the wood burning fire.

Top Guest favourite
A modern bungalow is framed by trees under a vibrant sunset sky. Outdoor seating, including Muskoka chairs, surrounds a firepit, while a putting green is positioned in the foreground, featuring multiple holes for practice.
Cottage in Huntsville
5 out of 5 average rating, 168 reviews

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.

Superhost
Cottage in Highlands East
4.91 out of 5 average rating, 350 reviews

Tranquil Minnicock Lake | Hot Tub & Lake Front

✨ Tranquil Minnicock Lake Escape ✨ Experience the "wow" factor 15 mins from Haliburton! 🌲 This luxury retreat features a clean, shallow shoreline perfect for swimming. 🏊‍♂️ The Highlights: Wellness: Private Hot Tub & peaceful Creek sounds Water: Kayaks, Pedal Boat & Life Jackets included Outdoors: Large Fire Pit, BBQ & Trekking Trails Included: Full Linens, Towels & Coffee Station ☕ 📡 Essentials: Wi-Fi, Washer/Dryer, TV & Sleds 🛷 STR License: STR25-00047

Guest favourite
Two black Adirondack chairs are positioned on a wooden dock, facing a serene lake at sunset. The water reflects soft hues of orange and pink, while the surrounding landscape remains silhouetted in the background, creating a tranquil scene.
Cottage in Huntsville
4.97 out of 5 average rating, 100 reviews

Four season cottage on Lake Vernon!

Cozy year-round lakefront home in Huntsville, Muskoka! This property is situated on Lake Vernon (only a 20 minute drive from town). It has 3 decks, a large dock with plenty of sun, a floating raft with a water slide, outdoor games, fire pit and a BBQ. The cottage is an enjoyable experience no matter what time of the year with close access to Algonquin Park, Arrowhead, The OFSC snowmobile trail and all that Huntsville has to offer.

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
4.93 out of 5 average rating, 135 reviews

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.

Top Guest favourite
An aerial view of the cottage nestled among tall green trees along the shoreline, with a private dock extending into the calm lake. A single kayak is visible on the water, highlighting the serene natural surroundings.
Cottage in Municipality Of Highlands East
4.97 out of 5 average rating, 224 reviews

Lake Cabin: Private, 6BR, HotTub, Sauna, GameRoom

Welcome to 360 Peninsula Oasis 840 feet of private shoreline. 360° lake views from every room. No neighbours — just crown land, open water, and your group. This is the cottage people talk about for years. Nestled on a stunning peninsula on Koshlong Lake in the Haliburton area, this fully renovated 6-bedroom, 3.5-bathroom retreat sits on 3.5 private acres surrounded by crown land on all sides. Only 3 hours from the GTA.

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
4.93 out of 5 average rating, 324 reviews

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.

Popular amenities for Cherry Island cottage rentals

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  2. Canada
  3. Ontario
  4. Muskoka
  5. Muskoka Lakes
  6. Cherry Island
  7. Cottage rentals