Holiday rentals in Gregory

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Top-rated holiday rentals in Gregory

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
Guest house in MacTier
5.0 out of 5 average rating, 17 reviews

Muskoka Nature Retreat A.C. & Fire Pit

🏡 Private guest suite above garage - hosts onsite 🔥 Use of fire pit available by request. 🛏️ Queen bed + twin bed available on request 📺 Smart TVs in living room & bedroom 📶 High-speed Wi-Fi + dedicated workspace 🍳 Kitchenette with coffee station, cookware & essentials 🛁 Private 4-piece bathroom 🧺 In-suite washer & dryer 🔥 Cozy indoor gas fireplace 🍽️ BBQ & private patio with outdoor seating 🚗 Parking with room for boats, UTVs & trailers 🇧🇷 Complimentary BJJ class Mon & Wed bookings

Guest favourite
Tiny home in Rosseau
4.91 out of 5 average rating, 175 reviews

Treehouse + cedar sauna

Perched atop a dramatic cliff overlooking a private pond, this one-of-a-kind off-grid treehouse is surrounded by acres of untouched forest and rugged rock cliffs. Designed for total privacy and tranquility, it’s the perfect place to unplug, slow down, and reconnect with nature. Spend your days canoeing or simply soaking in the peaceful views. As night falls, gather around the bonfire to roast marshmallows, unwind in your private sauna, and enjoy breathtaking stargazing far from city lights.

Top guest favourite
A modern two-story house is framed by tall trees, set against a backdrop of warm sunset hues. A stone driveway leads to the entrance, which is adorned with welcoming plants and porch lighting, creating an inviting entryway into the home.
Cabin in Huntsville
5.0 out of 5 average rating, 170 reviews

Cozy Cabin with hot tub, Sauna, hot yoga studio.

Welcome to D’oro Point overlooking Mary lake. We invite you to come relax, restore, and reconnect with nature on our 7.5 acres of wooded bliss. With only an approx 3 minute walk to our quaint neighbourhood beach, we are close enough to enjoy the lively lake life, yet maintain a private retreat feel. Stay on property and reap the health benefits of our private spa like amenities, which include the sauna, infrared hot yoga studio, and hot tub. Or, go out and explore all Muskoka has to offer.

Top guest favourite
A sunlit living space features large windows with views of the lake, allowing natural light to fill the room. A cozy striped armchair and a simple wooden coffee table are positioned on a wooden floor. A round table with decorative placemats complements the inviting atmosphere.
Cottage in Parry Sound
4.94 out of 5 average rating, 189 reviews

Muskoka Waterfront w/ Hot tub (Silver Linings)

*No extra fees* Come enjoy our designer furnished, newly-built, 4-season, Silver Lining Muskoka Lakehouse. This cottage offers you and your loved ones the perfect getaway with tons to do and memories to make with Insta sunsets over a lake wrapping around the entire property, a sandy beach to dip your toes, hot tub to warm up with friends, fire pit for roasting marshmallows. Other amenities: fully stocked kitchen, treehouse, games, BBQ, 1 acre of privacy, pet bed, well maintained hot tub.

Guest favourite
A spacious living area features large windows that provide ample natural light and views of the surrounding trees and water. A comfortable sectional sofa, a stylish leather couch, and a glass coffee table are arranged around a cozy wood stove, creating a welcoming atmosphere.
Home in Port Carling
4.89 out of 5 average rating, 159 reviews

Waterfront Boutique Cottage Getaway

Welcome to your cozy and relaxing cottage getaway in Muskoka. Situated on the serene waters of Bass Lake, explore the nearby town of Port Carling - known for its Snowmobiling Trails, Charming Shops, Restaurants, and stunning Lakeside View. A short walk to Bass Lake Roadhouse Restaurant. This home is surrounded by lush trees and stunning views of the water, it is the perfect blend of rustic charm and modern amenities to make your stay comfortable and enjoyable all year round.

Top guest favourite
A wooden dock extends over calm waters, featuring four Adirondack chairs in red and yellow. The serene lake reflects the surrounding trees and sky, with a light morning mist gently hovering above the water's surface.
Cottage in Port Carling
4.99 out of 5 average rating, 146 reviews

Gorgeous Muskoka Getaway on stunning private lake

Enjoy the perfect cozy Muskoka cottage "The Perch" on a beautiful private lake. This family and pet-friendly home is your year-round retreat. Your family will be close to everything when you stay at this centrally located place but you will feel like you are at a peaceful cottage surrounded by nature. With all of the amenities that you would need, you will find that The Perch is everything you are looking for to create memories with friends, families or a loved ones.

Top guest favourite
The cottage features a contemporary design with large glass windows, reflecting autumn foliage and the serene lake surrounding it. A deck offers outdoor seating with steps leading down to a small dock where canoes are moored, nestled among lush trees.
Treehouse in Utterson
4.96 out of 5 average rating, 256 reviews

The Water’s Edge * * Unique Muskoka Treehouse * *

CottageCreators presents a once-in-a-lifetime (or as often as you’d like!) Muskoka escape. Perched among the treetops on one of the region’s most stunning lakes, this rustic-luxury retreat offers a floating hammock net, two-sided indoor/outdoor fireplace, and private dock for swimming, canoeing, kayaking and SUP. Fall asleep to the gentle sounds of the lake, wake up to sunrise through the trees, and unwind in total seclusion—just you, the forest, and the water.

Guest favourite
A secluded treehouse is nestled among tall trees, showcasing a modern design featuring large windows and a sloped roof. The structure is elevated, supported by solid timber, and surrounded by fallen leaves, highlighting the natural beauty of the forested setting.
Treehouse in Dorset
4.96 out of 5 average rating, 315 reviews

Raven's Roost- private luxury treehouse with sauna

Unplug your tech and let the sights and sounds of the forest be your muse. Treat your body to the healing powers of a eucalyptus sauna. Cool down in the outdoor shower, stargaze, crack a book, play some Scrabble, colour or write. Sing with the wolves, skate through the forest, canoe, climb, swim, ski or snowmobile from your door to the OFSC trail. The quaint town of Dorset is in the center of one if Canada's most impressive landscapes. Escape. Exhale.

Top guest favourite
A serene waterfront view is presented from a deck, showcasing calm water surrounded by lush green trees. Comfortable seating arrangements are visible, creating a perfect spot for relaxation while enjoying the natural landscape.
Cottage in Torrance
4.97 out of 5 average rating, 253 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 favourite
Cabin in Huntsville
4.95 out of 5 average rating, 604 reviews

Aux Box Muskoka | Boutique | Private Nordic Spa

Escape to The Aux Box—a private boutique cabin nestled in the Muskoka woods with river views. Every amenity is exclusively yours, including the Nordic spa with a sauna, hot tub, cold plunge, and outdoor shower (summer). A short trail leads to your private dock with lounge chairs and canoe on the Muskoka River. Inside, enjoy custom cabinetry, a spa-inspired bathroom, and bespoke Canadian amenities, all just 10 minutes from downtown Huntsville.

Top guest favourite
A shaded exterior view of the cottage highlights a wooden deck extending towards the water. A towel hangs from a hook beside a window. Two white lounge chairs are positioned on the deck, with a hint of greenery from the surrounding trees reflecting in the calm lake.
Cottage in Parry Sound
4.95 out of 5 average rating, 75 reviews

Rockhaven Muskoka — Stunning Privacy!

Rockhaven is a quintessential yet modern cottage on 5 acres of land with 1600 feet of shoreline on a pristine, motor boat free private lake. Swim from the large dock or paddle the lake and look for wildlife. Enjoy sunrises, swimming, camp fires & BBQ's on the south east facing terraced deck or retreat to the games room on a rainy day for ping pong. — We operate from early May to early November. Summer Season: 7 night min, Sat-Sat.

Top guest favourite
Cabin in Sprucedale
5.0 out of 5 average rating, 127 reviews

Black Fox Cabin with Private Nordic Spa

Welcome to your serene escape in our brand new cabin! Nestled in a very private pine forest on a 6-acre lot, our modern cabin offers a full spa-like experience designed for ultimate relaxation and connection with nature. This tranquil retreat features a cozy firepit, a modern sauna with panoramic views, cold plunge and a rejuvenating hot tub. Perfect after a day of exploring the beautiful surroundings.

Popular amenities for Gregory holiday rentals

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