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Cottage vacation rentals in Cherry Island

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Top-rated cottage rentals in Cherry Island

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Top guest favorite
A charming A-frame chalet is set amidst a snowy landscape, with a green metal roof and large windows revealing forest views. A wooden deck with steps leads to the entrance, surrounded by birch and pine trees in a serene winter setting.
Cottage in Huntsville
4.98 out of 5 average rating, 399 reviews

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

Welcome to Muskoka A-frame, the perfect couple’s getaway or solo retreat. Relax in the *HOT TUB**. Wake up to swaying treetops, play boardgames & albums by the fire, with 2-story 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. Hike, snowshoe or cross-country ski Limberlost, ski/snowboard Hidden Valley, skate through Arrowhead forest & visit Huntsville for restaurants, breweries & local amenities

Top guest favorite
Cottage in Huntsville
5 out of 5 average rating, 283 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 favorite
Cottage in Bracebridge
4.89 out of 5 average rating, 116 reviews

Cozy Muskoka River Cottage - Canoe, BBQ, Fire Pit

Retreat in the heart of Muskoka, come enjoy the sparkling calm of Muskoka River. Inside offers an open concept kitchen, living and dining area and two bedrooms facing a forested backyard with a walk-out deck. Fire up the BBQ on the front patio or toast marshmallows by the river at your new waterside oasis. ☃️❄️ From ice skating trails, winter fests and tubing to dog sledding, snowshoeing and sleigh rides — winter at the cottage is exciting, tranquil and beautiful. Ask us for recommendations!

Guest favorite
Cottage in Utterson
4.94 out of 5 average rating, 238 reviews

Cozy Muskoka Winter Escape with 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 favorite
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, 144 reviews

Tiny Luxury Cottage with Hot Tub

This tiny luxury 2 bedroom cottage with loft 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 serene winter scene features a snow-covered driveway leading to a cozy cottage framed by tall pine trees. A dog sits peacefully in the foreground, with snow blanketing the ground and the cottage's welcoming windows visible in the background.
Cottage in Huntsville
4.95 out of 5 average rating, 110 reviews

Dog friendly Muskoka. Fun from forest to river.

Featured in Apartment Therapy and Cottage Life Magazine! Our beautiful cottage, nestled in Muskoka forest, is infused with Australian charm. Explore 300 acres of forest, walk to the river for a dip or simply bask in the sun on our deck. Books, magazines, games and puzzles are provided. We've furnished our cottage with mix of new and vintage pieces giving it a laid-back vibe. Swim in the Muskoka River in the warmer months, hike the forest year round and enjoy snowshoe trails in Winter.

Top guest favorite
The cozy cottage features a welcoming porch with white railings, surrounded by vibrant autumn foliage. The exterior showcases gray siding, with a prominent sign displaying 'Hudson.' A few pumpkins and decorative flowers are placed near the entrance, adding seasonal charm.
Cottage in Bracebridge
4.92 out of 5 average rating, 342 reviews

The Hudson - Riverside Cabin, Bracebridge

Nestled in the pines on the Muskoka River is this cozy one-bedroom cottage, ideal for a couple’s retreat. The Hudson offers the best of all worlds: it is relaxing, tranquil, and private, but you’re only a 10-minute drive from the Town of Bracebridge with unique shops, restaurants, groceries, and breweries, not to mention numerous tourist attractions. Marked trails are direct across the river. For more photos and information visit us on IG (at) thehudson.riversidecabin

Top guest favorite
A modern cottage surrounded by snow-covered trees is depicted, showcasing large windows that reflect the colorful sunset. A circular hot tub and outdoor seating are visible on the patio, enhancing the tranquil and cozy ambiance of the property.
Cottage in Huntsville
5 out of 5 average rating, 129 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 modern cottage is visible at the top of a sloping hill, framed by vibrant greenery. A wide set of wooden stairs leads from the dock area up to the cottage. Various watercraft, including kayaks and a canoe, are neatly arranged on the dock.
Cottage in Torrance
4.97 out of 5 average rating, 239 reviews

Beautiful Nine Mile Lake

Beautiful Muskoka getaway! Modern 4 season waterfront cottage! Stunning views! Located on picturesque Nine Mile Lake. Over 70% of the lake is crown land. Perfect for kayaking and canoeing to enjoy all the beauty Muskoka is known for. We have kayaks a canoe and a paddle board for you to enjoy. Plenty of sun exposure on the dock you can swim all day long. Close to hiking and snowmobile trails. May 15-Oct Minimum 6 nights with a Sunday check in.

Top guest favorite
Cottage in Township Of Muskoka Lakes
4.96 out of 5 average rating, 115 reviews

Stunning Muskoka Waterfront Cottage on 3 Mile Lake

Whispering Pines Cottage is a spacious 4-bedroom retreat on a private 2-acre property surrounded by 3 Mile Lake and the Dee River. Take in stunning winter lake views through the large Muskoka window, explore nearby snowmobile trails, or enjoy peaceful walks through the snowy landscape. The perfect Muskoka winter escape for families and nature lovers. Note: In winter months, all wheel drive vehicles with winter tires are mandatory.

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, 134 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.

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
4.94 out of 5 average rating, 285 reviews

D O C K | NEW Modern Muskoka Waterfront 2+1 bed

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

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