
Cottage holiday rentals in Cherry Island
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Top-rated cottage rentals in Cherry Island
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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.

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.

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! ✨

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.

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.

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.

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"

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.

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.

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.

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.

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
Cottage rentals with a hot tub

Private 40 Acre Cottage with Hot Tub

Waterfront cottage on quiet Spence lake

Charlie the Cottage | Hot Tub | Trail | Hike/Run

Cottage in Gravenhurst

Beautiful Lake House

The Hudson - Riverside Cabin, Bracebridge

Stunning Peninsula -Sandy beach | Hot tub & Sauna

Charming riverside cottage, B&B license
Pet-friendly cottage rentals

Charming cottage on Lake Muskoka

Muskoka Lakefront A-Frame | Sauna + Hot Tub

Waterfront 3 BR Cottage 4 Seasons Gravenhurst Heat

Peaceful Waters Cottage

Central & Charming Huntsville Cottage Retreat!

The Beach House, Georgian Bay, Beach View w/ Sauna

Stunning Bigwin Island Retreat

Muskoka Birch House-Hot Tub+Wood Burning Sauna+Gym
Private cottage rentals

Cozy Cottage on *Semi-Private Lake* ~ The Rosie ~

HarpHyggeHouse - Serene all-season lakefront

Four season lakefront cottage in Muskoka

Canfield House at Otter Lake Muskoka

Cottage in Huntsville, Muskoka. Hot tub + Sauna.

Lakefront Retreat-Mary Lake|Kayak, Canoe, Firepit|

Gorgeous Waterfront 4 Bdrm Classic Cottage Retreat

Raven’s Den Cottage in Haliburton
Destinations to explore
- Montreal Holiday rentals
- Greater Toronto and Hamilton Area Holiday rentals
- Greater Toronto Area Holiday rentals
- Mississauga Holiday rentals
- Island of Montreal Holiday rentals
- Northeast Ohio Holiday rentals
- Grand River Holiday rentals
- St. Catharines Holiday rentals
- Niagara Falls Holiday rentals
- Erie Canal Holiday rentals
- Detroit Holiday rentals
- Laurentides Holiday rentals
- Arrowhead Provincial Park
- Mount St. Louis Moonstone
- Hidden Valley Highlands Ski Area and Muskoka Ski Club
- Ontario Cottage Rentals
- Gull Lake
- Deerhurst Highlands Golf Course
- Lions Lookout
- Georgian Bay Islands National Park
- Torrance Barrens Dark Sky Conservation Area
- Three Mile Lake
- Kennisis Lake
- Menominee Lake
- Awenda Provincial Park
- Wye Marsh Wildlife Centre
- Kee To Bala
- Casino Rama Resort
- Haliburton Forest & Wild Life Reserve Ltd
- Bass Lake Provincial Park
- Limberlost Forest and Wildlife Reserve
- Fairy Lake
- Couchiching Beach Park
- Haliburton Sculpture Forest
- Dorset Lookout Tower
- South Muskoka Curling and Golf Club





