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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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Top guest favourite
A charming cabin nestled amidst vibrant autumn foliage, showcasing an array of red, yellow, and orange leaves. The waterfront view highlights the structure's outdoor deck and a boat garage, all reflecting a peaceful lakeside setting under a clear blue sky.
Cottage in Dwight
4.94 out of 5 average rating, 124 reviews

Muskoka Majesty The Sugarbush Cottage

Muskoka Majesty on Lake of Bays is situated on 2.2 Acers, and 170 feet of undisturbed, pristine, private waterfront. It is located 25min from Huntsville, Algonquin Park, and Hidden Valley Ski Resort. You can Hike, Bike, Swim, Boat, ​Golf, Fish, ATV, Snowmobile, Ski, and so much more. Enjoy the sights and attractions that this area has to offer. Visit the quaint towns​, shops and local artists, and artisans. Above all, take time to relax, enjoy each others company, and build beautiful memories.

Top guest favourite
A charming A-frame cabin is framed by lush trees, featuring a green metal roof and large windows that create a bright atmosphere. A wooden deck extends from the entrance, with a firepit surrounded by four Adirondack chairs positioned on a grassy area.
Cottage in Huntsville
4.98 out of 5 average rating, 441 reviews

Muskoka A-Frame + HOT TUB | Arrowhead | 4-Seasons

*MAY AVAILS* Welcome to Muskoka A-frame, the perfect couple’s getaway or solo retreat. Relax in the hot tub, roast marshmallows over a bonfire, wake up to swaying treetops & play boardgames & albums by the fire, to forest views. This classic 70’s A-frame cabin has been re-imagined for the modern world. Nest away or make it your base for 4-seasons of adventure. Explore Arrowhead & Limberlost forests, trails & beaches, or visit charming Huntsville for restaurants, breweries & local amenities.

Guest favourite
A hot tub is situated on a wooden deck, surrounded by lush greenery and mature trees. The clear water in the tub reflects the natural light, providing a tranquil setting for relaxation. A wooden privacy screen is positioned nearby, enhancing the serene atmosphere.
Cottage in Huntsville
4.99 out of 5 average rating, 300 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! ✨

Guest favourite
Four red Adirondack chairs are arranged neatly on a wooden dock beside the lake, with a large striped umbrella providing shade. The calm water reflects the lush greenery from the shoreline, creating a serene setting ideal for relaxation.
Cottage in Utterson
4.94 out of 5 average rating, 241 reviews

Summer Dates Now Available - Private Beach/Hot Tub

Welcome to the best Muskoka has to offer! Our 4-bedroom cottage is perched on a piece of the Canadian Shield with aerial views of the lake and a gentle slope down to your own private sandy beach. Explore 1.5 acres of beautiful wooded forest, play games on the flat manicured lawn or enjoy 245 feet of shoreline on the shallow sandy beach or jumping off the dock. Take in gorgeous sunsets from the large upper deck and toast marshmallows over the fire to end your evenings on Three Mile Lake.

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, 165 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.

Top guest favourite
Cottage in Utterson
4.9 out of 5 average rating, 117 reviews

Cozy Waterfront Lakehouse w/Sunset Views GLDN Days

Welcome to GLDN Days Lake House. A cozy, 820 sq. ft. cabin retreat, just 15 minutes north of downtown Huntsville, Muskoka. The Lake House is West facing with sunset views. Step onto the private dock and take a dive into a peaceful, non-motorized lake. The Lake House is ideally situated as it is both remote, but also conveniently located only a 5 minute drive off Hwy 11, with access to Hope's grocery store and LCBO at the exit. You'll have everything you need at your fingertips.

Top guest favourite
A paddleboard rests on calm waters near a wooden dock, leading to a spacious cottage nestled among trees. The back of the cottage is visible, showcasing an expansive deck that extends over the landscape. Natural vegetation surrounds the area, adding a serene touch.
Cottage in Huntsville
4.99 out of 5 average rating, 109 reviews

Huntsville Lakefront Luxury Cottage Retreat

***4 season, snow plowed road, and easy to access! *** Spectacular 4,000 sqft lakefront cottage on a private estate in beautiful Huntsville. The home has panoramic views of the lake. The great room boasts 22' high cathedral ceilings and a cozy gas fireplace. Enjoy a gorgeous fully stocked gourmet kitchen and a large dining room perfect for entertaining. This cottage is minutes to Algonquin park trails, Deerhurst Golf Course, Hidden Valley Ski club. STR License# "STR-2025-191"

Top guest favourite
The cottage exterior is framed by tall pine trees and features black siding with red shutters. Large windows reflect the surrounding landscape, while a gravel pathway leads to the entrance. The lush green yard extends towards the lakeside, providing a serene view.
Cottage in Burk's Falls
4.99 out of 5 average rating, 107 reviews

Rustic-chic Lake Side Cottage Getaway.

Unwind at our stunning lakeside guest cottage year round. A great destination for families and couples. Each season will gift you with beautiful vistas and experiences from water sports and fishing to hiking and snowmobiling. High pine ceilings, luxury appliances, and rustic details offer a luxurious yet charming feel. Enjoy the lake views and picturesque landscape from the cottage, deck, and dock. The cottage is located on spring fed Three Mile Lake in Katrine/Burks Falls.

Top guest favourite
The exterior of the cottage features a modern sauna made from wood, accented by a striking red circular door. Muskoka chairs are arranged nearby, while a firepit provides a cozy gathering spot. Lush greenery surrounds the property, with a vibrant sunset sky in the background.
Cottage in Huntsville
5 out of 5 average rating, 163 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.

Top guest favourite
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
A modern boathouse is situated on a tranquil lake, surrounded by tall trees. The building features multiple windows and a spacious deck on the roof, providing scenic views of the water. Sunlight reflects on the calm lake surface, enhancing the serene environment.
Cottage in Windermere
4.98 out of 5 average rating, 106 reviews

Lake Rosseau Boathouse Getaway for 2

Beautiful boathouse on Lake Rosseau. 650 square feet, 1 bedroom, 1 bath with kitchen and living space. Wrap around deck with stunning cliff and lake views. Bring your own boat, free public launch ramp next door. Easy dock access for swimming and to tie your boat. Enjoy boating, fishing and swimming on Muskoka’s “Big Three” lakes. Space is ideal for 2 adults. Additional adults (over 12) are $50/night each to a maximum of 4.

Guest favourite
A hot tub filled with bubbling water is positioned on a snowy deck, surrounded by tall evergreen trees. A serene view of the Muskoka River can be seen in the background, reflecting the soft light of the winter sky. Several outdoor chairs are arranged nearby.
Cottage in Baysville
4.93 out of 5 average rating, 318 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 cottage rentals in Cherry Island

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