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Cottage vacation 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 favorite
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 favorite
Cottage in Huntsville
5 out of 5 average rating, 145 reviews

Muskoka Lake Hideaway+ HOT TUB/Waterfront/Bonfires

*May & Summer AVAILS* The waterfront dock is up & ready for the season! Soak in the gazebo-covered hot tub to lake & forest views - rain or shine. Enjoy a bonfire, cozy up to the indoor gas fire with a book or board game & watch the seasons change over lake views. Welcome to Muskoka Lake Hideaway, a 4-season cottage for couples, a family getaway or small group of friends. For outdoor adventures, explore Arrowhead, Limberlost & visit Huntsville for restaurants, breweries & local amenities.

Top guest favorite
Cottage in Bracebridge
4.99 out of 5 average rating, 167 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 favorite
A cozy sitting area features two light-colored armchairs with soft cushions, positioned near large windows offering views of the trees and lake beyond. A small circular table sits between the chairs, enhancing the inviting space filled with natural light.
Cottage in Utterson
4.9 out of 5 average rating, 119 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 favorite
Double doors with large glass panels open to reveal a scenic view of Peninsula Lake. Light wood walls and a wooden floor complement flowing curtains, enhancing the warm space that invites natural light and tranquil lake views.
Cottage in Huntsville
4.97 out of 5 average rating, 273 reviews

Lakeview Cottage on Peninsula Lake

Lakeview Cottage on Peninsula Lake Located in Muskoka on beautiful Peninsula Lake with 200 feet of waterfront, this cottage has an amazing western view to watch evening sunsets. There is a sand beach with a gradual walk-in to swim and a dock. For the adventuresome there is a canoe, peddleboat and two kayaks. Also there is a fire pit, shuffleboard court and horseshoe pit. The cottage is close to Huntsville, Arrowhead and Algonquin Parks. No pets please...no exceptions.

Top guest favorite
A modern farmhouse-style cottage is framed by vibrant fall foliage. The exterior features a combination of white siding and natural stone, with a welcoming front porch and stone pathway leading to the entrance, set against a backdrop of red and orange leaves.
Cottage in Huntsville
5 out of 5 average rating, 166 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 favorite
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 favorite
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 favorite
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, 320 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.

Top guest favorite
A modern log cottage is viewed from above, featuring a large elevated deck with railings. The structure showcases a combination of dark wood siding and stone accents, with multiple windows allowing natural light. Surrounding greenery adds to the serene environment.
Cottage in Gravenhurst
4.96 out of 5 average rating, 117 reviews

Foster's Landing - Log Cottage on Lake Muskoka

Relax, play, or work from "Home" at this new Log Cottage on Lake Muskoka. The property features 3 bedrooms, a fully-featured kitchen, bathroom with rain shower, Great Room with seating, dining space and cathedral ceilings, a large elevated deck with BBQ, an additional large portion of covered deck, a basement laundry room with washer and dryer, and ample open spaces at the front, side, and rear of the cottage.

Guest favorite
Cottage in Township Of Muskoka Lakes
4.96 out of 5 average rating, 126 reviews

Stunning Muskoka Waterfront Cottage on 3 Mile Lake

SUMMER 2026 PROMOTIONS AVAILABLE - PLEASE MESSAGE FOR DETAILS. Whispering Pines Cottage is a private 4-bedroom Muskoka retreat on 2 acres with over 1,000 ft of waterfront on 3 Mile Lake and the Dee River. Enjoy stunning views through large Muskoka windows, a spacious Great Hall, fully equipped kitchen, and a lower level with entertainment. Ideal for families or longer, relaxing stays. STRA-TML-26-0046

Guest favorite
An aerial view of a cozy cabin nestled among tall trees, showcasing a wooden staircase leading to the waterfront. The deck is visible, with outdoor furniture set against a backdrop of lush greenery, while a peaceful shoreline is seen below.
Cottage in Bracebridge
4.84 out of 5 average rating, 176 reviews

Muskoka Waterfront Cabin w/ pool table&Falls view

Welcome to Fallsview Dream cottage! Enjoy the property’s STUNNING waterfront, hot tub, pool table & private beach This cozy cabin is perfect for those who love nature, privacy and the cottage life. Right in the middle of the woods with the most beautiful waterfall view. Watch the sunrise and sunset right from the deck surrounded by trees. Take the time to reconnect with your family/friends :)

Popular amenities for Cherry Island cottage rentals

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