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, 149 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

Guest favorite

A spacious living area features large windows that provide views of the surrounding trees and Muskoka Lake. Comfortable seating is arranged around a central coffee table, with decorative pillows and a rug adding warmth to the space. A BBQ grill is visible on the deck outside.

Home in Port Carling

5 out of 5 average rating, 15 reviews

Villa Marina Haven|BBQ|Firepit|Waterfront|Cozy

Welcome to your perfect escape in the heart of Port Carling! This charming cottage offers the ideal blend of convenience and relaxation, providing a peaceful haven for those looking to unwind and explore the beauty of the Muskoka region. Our cozy retreat is nestled in a serene setting, offering a tranquil atmosphere surrounded by nature. Whether you're planning a romantic getaway or a family vacation, this delightful cottage caters to all. !!!!!MUST HAVE GOOD WINTER TIRE FOR WINTER ACCESS!!!!

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, 244 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.

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, 39 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

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

4.92 out of 5 average rating, 141 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.

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, 194 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 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, 124 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, 115 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

4.95 out of 5 average rating, 176 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

The cottage is positioned by the tranquil waters of Henshaw Lake, showcasing a sandy beach area. A kayak rests on the lake, surrounded by lush greenery and tall trees. The inviting exterior of the cottage features large windows that overlook the waterfront.

Cottage in Port Carling

5 out of 5 average rating, 55 reviews

Panoramic Lakeviews w/ Private Beach, Kayak, SUP

Escape to THE HENNY located on Henshaw Lake, Port Carling Muskoka. 3-4 BD (beach bunkie available May-Sept). Panoramic lake views + sunsets! Completely private & secluded. Enjoy your very own private beach w/ 665ft of waterfront. Soft, sandy beach, shallow entry, clean water for swimming. Perfect for families. Paddle boards, canoe, kayak, water lily. BBQ, fire pit + wood burning fireplace. Steps to hiking, waterfalls, wine tasting, waterskiing. Sleeps 6-8

Top guest favorite

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, 232 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 2 Minimum 6 nights with a Sunday check in.

Superhost

A wooden dock extends out over a tranquil lake, where gentle ripples reflect sunlight. A canoe rests on the dock, with trees lining the opposite shore, showcasing hints of autumn colors.

Cabin in MacTier

5 out of 5 average rating, 4 reviews

Priscillas Too on Bass Lake

Escape to this charming cabin in MacTier, Ontario, nestled on the stunning shores of Bass Lake. Enjoy breathtaking sunset views from your private waterfront access, perfect for swimming, fishing, and creating lasting memories. With comfortable accommodations, a fully equipped kitchen, and a cozy indoor fireplace, this family-friendly retreat offers the ultimate relaxation. Explore nearby attractions and embrace the beauty of the Canadian Shield.