Vacation rentals in Gregory

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Top-rated vacation rentals in Gregory

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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, 55 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, 269 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, 111 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!

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, 211 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.

Top guest favorite

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, 128 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 spa like amenities, which include the sauna, infrared yoga studio, and new hot tub. Or, go out and explore all Muskoka has to offer.

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, 475 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, 128 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.

Top guest favorite

A bright living area encompasses a comfortable seating arrangement with a blue armchair and natural wood chairs around a circular dining table. A stone fireplace with decorative elements serves as a focal point, while light flows through large windows adorned with sheer curtains.

Home in Port Carling

5 out of 5 average rating, 10 reviews

Port Carling - Muskoka Mornings 2-bedroom home

Charming 2-bedroom main level of home in the heart of Port Carling, perfect for business travelers and vacationers. Enjoy a full kitchen, BBQ, in-unit laundry, and a delightful three-season sunroom. Central location with walking distance close to shopping, dining, and Hospice Muskoka. Home away from home stays with high-speed Wi-Fi and ample parking. Experience comfort and convenience in this cozy retreat. Book now for a memorable stay!