Holiday houses in Gregory

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Top-rated holiday rentals in Gregory

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Guest favourite
A spacious glamping dome is nestled among lush green trees, showcasing large windows and a triangular design. The entrance is framed by rustic outdoor seating, and soft lighting emanates from inside, creating an inviting atmosphere amidst the surrounding foliage.
Dome in Utopia
4.95 out of 5 average rating, 266 reviews

Off-grid Glamping Dome Nestled in the Woods

Welcome to our private campsite in Utopia, ON. Our family’s glamping dome is your chance to experience a unique getaway surrounded by the sights & sounds of nature. Amenities include camping essentials & some glamping perks: king size bed, bbq, fireplace, Indoor incineration toilet, soap & water, outdoor shower (summer only), kettle, cooking utensils. Nearby is Purple Hill Lavender Farms, Drysdale's Tree Farm, Tiffin Conservation Area, Nottawasaga & golf courses. Wasaga Beach is 30 min away.

Top Guest favourite
Cabin in Huntsville
4.95 out of 5 average rating, 584 reviews

Aux Box Muskoka | Boutique | Private Nordic Spa

Escape to the Aux Box, a boutique luxury cabin nestled in the Muskoka woods with serene river views. Designed for comfort and style, it features in-floor heating, custom cabinetry, and premium amenities. Step into your private Nordic Spa with a sauna, hot tub, and cold plunge for the ultimate relaxation. Enjoy total seclusion while being less than 10 minutes from the shops, dining, and charm of downtown Huntsville. COMING SOON: waterfront access with private dock, lounge chairs and a canoe.

Guest favourite
Tiny home in Rosseau
4.91 out of 5 average rating, 150 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 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, 298 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! ✨

Superhost
Cottage in Muskoka Lakes
4.84 out of 5 average rating, 159 reviews

Muskoka Gem on 5 Acres of Enchanted Forest w/sauna

MUSKOKA! Directly on snowmobile trail! Modern & at the heart of it all. 5 acres of private forestland. Organic amenities, incl. a 6 person dome sauna! Private use of Trampoline, slackline, jungle gym, bbq, fire pit, games, books, Nintendo & more! Close to nature trails, lakes, beaches, parks, grocery, LCBO and pubs! The cottage is split into two separate units w/ separate amenities on opposite sides. We live on one side. Your stay is 100% private and does not have any internal access to ours.

Top Guest favourite
Cabin in Bracebridge
4.98 out of 5 average rating, 177 reviews

Cozy Cabin Getaway Muskoka

Escape to this 4 season Muskoka Cabin nestled in the forest to disconnect and reconnect with yourself & loved ones. Surrounded by nature, this rural home is located on 2.67 acres within the forest & woods. Peace and quiet awaits you. We are a 5 minute drive to Lake Muskoka with public beach, boat launch & dock. You may choose to simply hide away or venture out to see all Muskoka has to offer. ❄️ We are Christmas themed in the cabin Nov-Jan Follow us on insta! @cozycabingetaway_Muskoka

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 out of 5 average rating, 156 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, 180 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 screened porch is illuminated by soft lighting, featuring an outdoor sofa adorned with colorful cushions and a large swing chair. A propane fireplace provides warmth, and potted plants enhance the natural ambiance, creating a relaxing space for enjoying the evening.
Farm stay in Gravenhurst
4.96 out of 5 average rating, 522 reviews

Stix N Stones (Includes Light Breakfast & Kayaks)

Nestled in the woods on Walkers Point, this is a great opportunity to reconnect with nature. We promise when you leave you’ll appreciate the forest as much as the water that surrounds us. Although we are not on the water, we are a 3min drive to a semi-private beach. Kayaks & life vests included (& delivered). Snowshoes incl in winter. Light breakfast is yogurt & fruit. Short distance to renowned hiking trails, Hardy Lake Park, Sawdust City & Clearlake Brewery, Muskoka Winery.

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, 154 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, 138 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.

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, 300 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.

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