Holiday rentals in Gregory

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Top-rated holiday rentals in Gregory

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Top guest favourite
A modest basement unit is shown nestled within a snowy landscape, surrounded by tall trees. The structure features a ramp leading to a wooden deck, with snow blanketing the ground and partial sunlight illuminating the scene.
Place to stay in Port Carling
4.95 out of 5 average rating, 101 reviews

Basement Studio Apt - Hidden Gem In Muskoka!

Studio apt. basement unit in Minett, Muskoka. 3km to JW Marriott & The Rock. 15min to Port Carling, 20min to Town of Rosseau. A 350m walk to public beach on Lake Rosseau. Private unit incl. kitchen w/ hot plate, toaster oven, fridge, Nespresso coffee machine, kettle, utensils. 1 queen bed, linen & towels. Self Check-in. Free parking and Wifi. Smart TV. 28 min to ON Northland bus. To Note: Additional mattress available upon request. Unit has colder cement floor, sanitized indoor shoes provided.

Guest favourite
A spacious outdoor balcony features a wooden deck with a green and white patterned rug. Two chairs are positioned around a glass-top table, surrounded by lush greenery from neighboring trees. A large window on the wall offers natural light to the space.
Flat in Midland
4.9 out of 5 average rating, 130 reviews

Loft By The Bay

Welcome to our charming second storey apartment in downtown Midland, Ontario. This cozy space features a bedroom, office with futon, full kitchen, bathroom, laundry, and a bright open concept living area. Enjoy easy access to local shops, restaurants, and attractions. Explore the picturesque waterfront and nearby hiking trails. Retreat to this comfortable and inviting apartment after a day of work or play. Book your stay today for a convenient, comfortable, and memorable experience in Midland.

Guest favourite
A charming exterior of a dark-colored house is framed by lush green grass and two flowering trees. The trees display vibrant pink blossoms, contributing to a serene outdoor ambiance. The setting is brightened by clear blue skies and soft sunlight.
Cottage in Bracebridge
4.97 out of 5 average rating, 275 reviews

Century Home in Bracebridge Muskoka w/ EV charger!

Welcome to Century Charm, in Bracebridge, Muskoka! We are located right in the heart of Bracebridge. Located across the street from the Muskoka river, steps to Bracebridge Falls and within 6 minute walk from the historic downtown core. Walking distance to Muskoka Brewery. Kirby’s Beach & Bowyers beach nearby, 5 minutes from Santa’s village, 10 minute drive to Bracebridge Resource Management and within 30 min drive to beautiful Arrowhead Provincial Park! Golf lovers, 19 golf courses nearby

Guest favourite
An outdoor seating area is illuminated by a fire table, featuring flames flickering above smooth stones. Two stylish chairs provide a cozy atmosphere, with a view of indoor greenery and decor through large windows. A barbecue grill is positioned nearby, enhancing the outdoor dining experience.
Cottage in Bracebridge
4.89 out of 5 average rating, 126 reviews

Cozy Muskoka River Cottage - Canoe, BBQ, Fire Pit

Retreat in the heart of Muskoka, come enjoy the sparkling calm of Muskoka River. Inside offers an open concept kitchen, living and dining area and two bedrooms facing a forested backyard with a walk-out deck. Fire up the BBQ on the front patio or toast marshmallows by the river at your new waterside oasis. ☃️❄️ From ice skating trails, winter fests and tubing to dog sledding, snowshoeing and sleigh rides — winter at the cottage is exciting, tranquil and beautiful. Ask us for recommendations!

Guest favourite
The interior of a cedar sauna features rounded wooden walls and benches. A large circular window offers a view of a snowy forest, enhancing the serene atmosphere. Natural light filters softly through the frosted glass, creating a calming space for relaxation.
Cottage in Muskoka Lakes
4.85 out of 5 average rating, 150 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.

Top guest favourite
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, 247 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 favourite
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, 510 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.

Top guest favourite
Cottage in Port Carling
4.99 out of 5 average rating, 137 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 favourite
An outdoor lounge area is covered by a large umbrella, featuring a cozy swing chair and cushioned seating. A chiminea and a stack of firewood are present, while vibrant flowers and lush greenery surround the space, creating a serene environment for relaxation.
Flat in Bracebridge
4.94 out of 5 average rating, 108 reviews

Muskoka Get Away-Romance & Adventure Awaits !!!

Newly renovated KING SIZE Cozy, Romantic & Stylish. Ideal for long term stays. Grab a book and curl up into the big comfy swing chair by the fireside of the chiminea on your private patio. Start your day off with a Nespresso in the outdoor lounge area surrounded by lush forest and all the nature your eyes & ears can behold. Grab a snack or whip up a gourmet meal in your fully equipped kitchen. And then at days end stretch out onto your very own King size sleigh bed!

Top guest favourite
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.
Loft in Parry Sound
4.95 out of 5 average rating, 307 reviews

Private Barn style loft king bed

Enjoy your own private loft retreat above a charming barn-style garage, thoughtfully equipped for a comfortable and relaxing stay. This cozy little getaway is just a short 3-minute walk or drive to two beautiful lakes with public beaches and boat launches, and only a quick 7-minute drive to Parry Sound for restaurants, shops, and local charm. A 24-hour convenience store and gas station are also nearby, making it the perfect peaceful spot to unwind and explore the area.

Top guest favourite
An aerial view showcases the cottage nestled among vibrant autumn foliage, featuring shades of orange, yellow, and green. The property is bordered by two bodies of water, one visible on the left. The distinctive red roof contrasts with the natural colors of the surrounding landscape.
Cottage in Township Of Muskoka Lakes
4.96 out of 5 average rating, 122 reviews

Stunning Muskoka Waterfront Cottage on 3 Mile Lake

Whispering Pines Cottage is a spacious 4-bedroom retreat on a private 2-acre property surrounded by 3 Mile Lake and the Dee River. Take in stunning winter lake views through the large Muskoka window, explore nearby snowmobile trails, or enjoy peaceful walks through the snowy landscape. The perfect Muskoka winter escape for families and nature lovers. Note: In winter months, all wheel drive vehicles with winter tires are mandatory.

Top guest favourite
A welcoming living area features a spacious sofa draped with soft blankets. A modern kitchen with white cabinetry and stainless steel appliances is visible. A cozy fireplace adds warmth, while large windows provide natural light, leading to a door opening to an outdoor space.
Flat in Coldwater
4.97 out of 5 average rating, 125 reviews

Cozy getaway for two with hot tub!

Unwind in our peaceful guest suite attached to our home located near Mount St-Louis Moonstone, Vetta Nordic Spa and the cozy town of Coldwater. With its private entrance, hot tub (accessible daily between 8am and 10pm) and serene forest surroundings, this space is designed for guests who value calm, quiet and nature. We ask that guests share our appreciation for a tranquil environment.

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