Vacation rentals in Gregory

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Top-rated vacation rentals in Gregory

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Top guest favorite

The exterior of the A-frame cabin is visible, set among greenery and trees. A spacious wooden deck features seating options, while two black chairs are positioned nearby on a natural landscape covered in fallen leaves.

Cabin in Bracebridge

4.97 out of 5 average rating, 157 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 favorite

A vibrant sitting area showcases a deep red sofa with patterned cushions, complemented by a colorful armchair. A wooden coffee table sits in the center, while a lamp and artwork enhance the cozy ambiance. Large windows provide ample natural light and views of the outdoors.

Apartment in Port Carling

4.96 out of 5 average rating, 53 reviews

Caledon, Mirror Lake (Lake Muskoka)Caledonia House

Welcome to your waterfront oasis on the stunning shores of Lake Muskoka! Experience the perfect blend of history and modern luxury at Caledon, our newly renovated self-contained upstairs apartment suite. Immerse yourself in the rich history of this property, dating back to 1928, while indulging in all the comforts of contemporary living. Step onto your private balcony and soak in breathtaking views of the lake, or take a stroll to town for fine dining, boutique shopping, and local attractions.

Top guest favorite

A charming two-story home with a red front door is surrounded by greenery. The front porch features multiple windows, allowing ample light. A stone pathway leads to the door, flanked by well-maintained shrubs and flowerbeds, enhancing the inviting entrance.

Home in Port Carling

4.97 out of 5 average rating, 65 reviews

The Bailey House in the hub of Muskoka lakes

Enjoy a quaint century home in the heart of Muskoka. Quiet location. Perfect for families. Just steps to the public boat launch, and beach with shallow entry for swimming and paddle sports. A large park with a castle playground your kids will love. A 10 min. walk takes you downtown, which boasts a variety of shops and restaurants. Or, enjoy all the beauty and activities Muskoka has to offer through the winter. Message for special packages or special celebrations or request items for arrival.

Guest favorite

The exterior of a barn-style loft is showcased, featuring a charming design with white vertical siding and a wooden double door. Large windows allow natural light to enter, while the surrounding landscape includes trees and autumn foliage, creating a serene atmosphere.

Barn in Parry Sound

4.95 out of 5 average rating, 267 reviews

KING SIZE BED Barn style loft apartment private

Very private apartment that you will have all to yourself that’s above a barn style garage. It has everything you need for a very comfortable stay. The perfect little getaway situated near 2 lakes with public beaches and boat launches with in a short 3 minute walking distance or even shorter drive. Parry sounds 7 minutes away. there’s Restaurants near by and there’s also a 24 hour convenient store/gas station near by! The locations very nice to relax and explore what the area has to offer.

Guest favorite

The exterior of the A-frame home is showcased, featuring a striking black facade and tall triangular roof. Large windows illuminate the interior, and a spacious wooden deck extends across the front, surrounded by lush greenery that encapsulates the natural setting.

Home in Georgian Bay

4.97 out of 5 average rating, 109 reviews

A-Frame in the Woods of GeorgianBay, Muskoka

Welcome to our A-frame in the heart of Georgian Bay, Ontario! Perfect for family escapes and relaxing couples weekends in Muskoka. This cozy retreat has three bedrooms and accommodates up to six guests. With Six Mile Lake and Whites Bay just a stroll away, indulge in serene swims or explore the local golfing, breweries, and skiing at Mount St. Louis. Immerse yourself in nature's embrace while relishing the comforts of our picturesque A-Frame home—a perfect family getaway for every season!

Top guest favorite

A handcrafted timber frame cabin is set among trees, featuring natural wood siding and large windows that invite the outdoors in. A welcoming porch is accessed by a wooden staircase, while a covered area to the side provides shelter. The surrounding forest complements the rustic design.

Cabin in Bracebridge

5 out of 5 average rating, 210 reviews

Secluded Lakeside Retreat - Atkins Hideaway

Tucked in the heart of Muskoka, this handcrafted timber frame cabin rests alongside a scenic spring-fed lake, surrounded by 8 acres of private forest. Only 10 minutes from Bracebridge, enjoy serene lake life and natural beauty while remaining close to town amenities, local shops, and eateries. Enjoy private dock relaxation, cozy cabin comforts, and outdoor fires. A Provincial Park Day Pass is included (*security deposit required) for added adventure. Come relax, recharge and reconnect.

Guest favorite

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, 474 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.

Superhost

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

4.88 out of 5 average rating, 129 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 favorite

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, 126 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 favorite

A two-story private residence is nestled among lush greenery, showcasing a charming green exterior. The large windows allow natural light to fill the space, while a wrap-around balcony offers outdoor seating. The entrance is elevated, accessed by a set of steps leading from the rocky landscape.

Cottage in Port Carling

4.98 out of 5 average rating, 178 reviews

Lake Muskoka Classic Cottage w/ Hot Tub

Start planning your retreat at this four season luxury private residence on lake Muskoka. Located in the heart of Muskoka’s pristine natural beauty. Relax and enjoy a truly unforgettable experience from the moment you arrive and create life long memories with loved ones. Home features a chef kitchen, butlers pantry, cozy double sided wood burning fireplace, heated floors in bathrooms, wrap around balcony, complete privacy from neighbours. Additional services available.

Guest favorite

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, 224 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 favorite

An open living space is highlighted by a prominent canoe hanging from the ceiling, with large windows allowing natural light. A glass dining table is set for six, complemented by contemporary black chairs. A spacious sectional sofa and wall-mounted TV are visible in the background.

Place to stay in Port Carling

4.92 out of 5 average rating, 59 reviews

Duke’s Boathouse Waterfront Apartment with Dock

Beautiful boathouse loft on the second floor of the historic Duke's building. Located right on the water in Muskoka, in downtown Port Carling in the middle of the action, but with lots of privacy. Perfect for those wishing to discover Muskoka, Re-visit Muskoka, Host family and friends for meals or have some privacy while visiting friends or family on the Muskoka Lakes. Park your car and travel with your own (or rented) boat, park at dock.