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, 153 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 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, 63 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.

Superhost

The interior of a cedar sauna features wooden benches arranged around a circular window, offering a view of the lush forest outside. Soft towels and a wooden bucket are placed on a central table, emphasizing the serene, natural ambiance.

Cottage in Muskoka Lakes

4.85 out of 5 average rating, 144 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.

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, 263 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, 106 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

An aerial view captures a cottage surrounded by vibrant autumn foliage, showcasing bright oranges and yellows. The nearby lake reflects the colorful trees, and a wooden dock extends toward the water. The serene environment emphasizes the natural beauty of the location.

Cottage in MacTier

5 out of 5 average rating, 42 reviews

Gorgeous Muskoka Lakes Cottage with Amazing Views

*PLEASE PUT THROUGH INQUIRY BEFORE REQUESTING* Welcome to Birch Haven with million dollar views inside & out! Located on the coveted Bass Lake in Muskoka. You'll be welcomed with bright & airy surroundings the minute you enter this charming cottage. Take in the pine accents, beautiful beams, cozy wood burning fireplace & windows abound with views for miles. Experience serenity at this family retreat & enjoy the shallow, gradual walk in sandy shoreline. Less than 2 hours away from Toronto.

Guest favorite

Two red adirondack chairs are positioned facing the tranquil Moon River, offering a scenic view of the water. Surrounding the chairs are lush trees and rocks, creating a peaceful outdoor space. Steps lead down to the water's edge, enhancing access to the lakeside.

Cottage in Bala

4.92 out of 5 average rating, 157 reviews

Charming Lakefront Bala Cottage

This charming, cozy, 4 season cottage overlooks the Moon River in the heart of Bala, just 12 minutes off the 400! With over a half-acre of land, this gem is located within minutes to the grocery store, Don’s Bakery, Beer Store, LCBO, The Kee, markets, the beach, hiking trails, snowmobile trails & more. 2 minutes to Bala (15 min walk) 10 minutes to Port Carling 15 minutes to Gravenhurst 25 minutes to Bracebridge Cottage is fully equipped for you to enjoy, just bring your personal items!

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, 202 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, 466 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

4.89 out of 5 average rating, 126 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, 123 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 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, 177 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.