Vacation rentals in Gregory

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Top-rated vacation rentals in Gregory

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Guest favorite

A spacious common area features a large, light-colored sectional sofa arranged around a warm fireplace built into a stone wall. Large glass doors provide access to a serene outdoor space, while natural light enhances the wood-beamed ceiling. Decorative elements include woven wall art and a wooden side table.

Cabin in Tiny

5 out of 5 average rating, 12 reviews

The Beach House, Georgian Bay, Beach View w/ Sauna

New!! A rare and stunningly designed cabin overlooking a semi-private beach on Georgian Bay. This tranquil 4-bedroom, 2-bathroom retreat is surrounded by trees with breathtaking views of the pristine bay. Every detail has been thoughtfully curated for your ultimate enjoyment. We include all linens, towels, sheets, firewood for in/outdoor fires, olive oil, salt, pepper, a fully equipped kitchen with utensils, PrimeTV, Netflix, Sonos, and more. Additionally, we are taking bookings for 28+ nights.

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, 253 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

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

4.99 out of 5 average rating, 100 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, 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, 143 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, 197 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 stone pathway meanders toward the cottage, bordered by lush greenery and towering trees. Prominent boulders create a natural landscape, providing a rustic charm. The cottage, featuring a brown exterior and wooden accents, is nestled among the serene surroundings with glimpses of the water visible in the background.

Cottage in MacTier

5 out of 5 average rating, 31 reviews

The Point - 6 bed, lake/fire pit/games room/wifi

Large main cottage with 3 bedrooms, 2 baths, open concept main floor with modern kitchen and a glassed in dining room over the lake. Large living room with fireplace. Lower level games room with darts, foosball, board games and a large TV with walkout to the dock. Main floor has a large wrap around deck with bbq. AMAZING separate cabin (50 feet from the main cottage) with 2 bedrooms plus loft, kitchenette, bathroom, sitting area and deck overlooking the lake. Excellent for families.

Guest favorite

A cozy studio room features two beds with distinct bedding patterns, complemented by wooden log walls. Natural light filters through various windows, enhancing the warm ambiance. A wooden chair and bedside table with a lamp offer practical comfort within the inviting space.

Guesthouse in Utterson

4.93 out of 5 average rating, 177 reviews

Lakefront Muskokan Log Cabin

In the heart of Muskoka on 3 Mile Lake. This cozy Log Cabin is set on private property. This studio room has all modern amenities which include 65” Smart TV, Netflix, microwave, keurig coffee maker, mini-fridge, toaster-oven, hot plate, barbecue and wall mounted fireplace. It has two beds and a full bathroom with seated shower. The waterfront has a shallow entry or you can jump in from the dock. A canoe, 2 kayaks & life jackets are for your use. End your night with a campfire.

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, 120 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, 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.

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, 56 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