Holiday rentals in Flesherton

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Top-rated holiday rentals in Flesherton

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Guest favourite
A camping area is illuminated by warm string lights, with two wooden chairs positioned near a fire pit. The glamping dome, partially visible in the background, is nestled among tall trees, creating a serene atmosphere in the woods at night.
Dome in Utopia
4.95 out of 5 average rating, 270 reviews

Off-grid Glamping Dome Nestled in the Woods

Welcome to our private campsite in Utopia, ON. Our family’s glamping dome is your chance to experience a unique getaway surrounded by the sights & sounds of nature. Amenities include camping essentials & some glamping perks: king size bed, bbq, fireplace, Indoor incineration toilet, soap & water, outdoor shower (summer only), kettle, cooking utensils. Nearby is Purple Hill Lavender Farms, Drysdale's Tree Farm, Tiffin Conservation Area, Nottawasaga & golf courses. Wasaga Beach is 30 min away.

Top guest favourite
A modern cottage features a stone exterior with a sloped roof, harmoniously blending into the surrounding forest. A cozy propane fireplace is visible on the patio, which overlooks a gently flowing stream bordered by smooth stones and lush greenery.
Cottage in Southgate
4.99 out of 5 average rating, 173 reviews

Luxurious Creek Retreat With Hot Tub

Welcome to this luxury cottage on the water. The perfect place to relax and unwind while listening to the waterfall and babbling brook flowing past only a few feet away. If you're looking for privacy and tranquility along with all the pleasures of a luxury stay then look no further. This property boasts a propane fireplace inside as well as one outside, in-floor heat and A/C. Fully equipped kitchen, two bedrooms with hotel quality mattresses and a bathroom that exudes high-end style and decor.

Top guest favourite
The rustic exterior of High Pines Cottage is highlighted by large, floor-to-ceiling windows that allow natural light to fill the interior. Surrounding the cottage, a well-tended garden features a variety of plants, stones, and landscaping elements, adding to the inviting allure of the property.
Chalet in Flesherton
4.97 out of 5 average rating, 86 reviews

Cozy cottage in the woods near trails & waterfalls

High Pines Cottage is a spacious yet cozy, pet friendly retreat. Located on a beautiful 1.8 acre lot that hosts a variety of large pines and other beautiful trees, it offers privacy and relaxation. It is perfect for any season with many activities from hiking to skiing and has a home gym. Whether you are looking to curl up by the fireplace or enjoy the trails with your pup, our cottage offers what you need to unwind or connect with friends and family. Check out Instagr. @high_pines_cottage

Top guest favourite
Place to stay in Chatsworth
5 out of 5 average rating, 127 reviews

Secluded Cabin overlooking Valley.

Our comfy one-room cabin sits on the edge of 40 wooded acres, overlooking a pastoral valley. Enjoy a relaxing breakfast (included) on the deck while taking in the countryside view, and in the evening, lose yourself in the deep, dark, star-studded sapphire sky. A great home base as you experience the area - hiking beaches, waterfalls, cideries, vineyards and wineries. See more things to do at visitgrey. ca. Or stay put and enjoy your secluded getaway. Read a book, take a hike, or have a nap.

Guest favourite
The cabin is nestled among trees, featuring a spacious deck with a sitting area. A hot tub is positioned nearby, while string lights create a warm ambiance. The exterior showcases large windows that invite natural light into the living space.
Place to stay in Southgate
4.99 out of 5 average rating, 283 reviews

Aframe cabin by babbling brook with sauna & hottub

Cabin partially OFF GRID in winter months (Nov 1-May 7) No running water/shower/indoor bathroom at this time. Water is provided with water dispenser/maintained outhouse *Wood hot tub replaced in 2025 with nordic spa *Cabin situated on heavily treed 1 acre property with a creek directly in front of a quiet municipal road *Wood stove remains off-limits during the summer season (June-September). Wood & kindling provided for fall/winter use *No firewood provided for firepit/guests to pick up

Top guest favourite
The entrance of a yurt is featured, showcasing a wooden deck with a decorative orange door. The circular structure is surrounded by lush greenery, highlighting the natural setting. Soft light filters through the trees, creating a peaceful outdoor environment.
Yurt in Meaford
4.99 out of 5 average rating, 188 reviews

Quiet Retreat for Two

Spend a starry night in the country with the comfort of a soft bed, a wood stove, and plenty of space both indoors and out. Our yurt is located in a pocket of trees next to rolling farm fields and beautiful conservation land that the Rocklyn creek meanders through. You can prepare your meals in a sweet outdoor kitchen that is entirely screened in- or choose to sit by the fire. Bruce Trail access is just around the corner, and the towns of Meaford and Owen Sound are a short scenic drive away.

Top guest favourite
A rustic wooden bridge spans a gently flowing stream, surrounded by lush greenery and tall trees. A manicured lawn is visible in the background, featuring multiple seating options. The water reflects the natural landscape, enhancing the serene ambiance of the setting.
Cabin in Kimberley
4.99 out of 5 average rating, 94 reviews

Luxury Creekside Cabin with Sauna

Exclusive luxury retreat! Creekside Cabin is the perfect couples escape to nature! This newly renovated gem is nestled in the forest calling you to unwind, refresh and to rejuvenate. Creekside is a fully licensed private property will instantly welcome you with peaceful sounds of cascading streams and waterfalls. Surrounding the beautiful pond, the forest setting is home to an array of wildlife including spotted deer, blue heron and even the beautiful snowy owl casually passing through.

Top guest favourite
Cabin in Ravenna
5 out of 5 average rating, 63 reviews

Hytte Away - Cabin Retreat with Sauna

We welcome you to Hytte Away, a thoughtfully designed private cabin retreat for two nestled on 54 acres of forest land. Offering you the opportunity to disconnect and reconnect. The property features an amazing sauna and cold plunge experience, hiking trails (currently being worked on from ice storm) and the perfect little cabin to do some actual relaxing. The space is unique and the best approach is to think of it as a glamping experience. Follow us on insta for more - hytteaway

Top guest favourite
Guest suite in Kimberley
4.94 out of 5 average rating, 827 reviews

The Post Office Motel & Spa in the ❤️ of Kimberley

*NEW HOT TUB* Located in the center of Kimberley downtown, a scene straight out of a hallmark movie. Watch the seasons come & go while taking in mtn views and soaking in the hot tub as stars line the night sky.Enjoy marshmallows by the 🔥, amidst this whimsical fortress.Walk to the General Store pick up fresh baked goods and breakfast supplies. Then the dinner choice is yours; Hearts Tavern or Justin’s Oven both just steps away. Bruce trail access at the door. The perfect slow down🌿

Top guest favourite
Tiny home in Arthur
4.97 out of 5 average rating, 392 reviews

Luxury tiny home on peaceful country estate

Escape to Heirloom Tiny Home - where macro luxury meets a micro footprint. Nestled on 23 peaceful acres, surrounded by aspen and pine forests, just 10 minutes from the picturesque town of Elora. Wake up to serene pond views as horses and sheep graze in your view. Organic linens, artisanal soaps, and a spa-like bathroom soothe the senses. Cozy up by the indoor fire and gaze at the stars. Enjoy fine dining at the Elora Mill and Spa, enjoy popular shops or hike the Elora Gorge nearby.

Top guest favourite
A serene lakeside view is presented as the sun sets, casting vibrant orange and pink hues across the sky and reflecting on the water. A small dock is visible, with several red Adirondack chairs arranged on the grassy area, inviting relaxation.
Cottage in Flesherton
4.95 out of 5 average rating, 150 reviews

All-Season Cottage on the Lake

An entire cottage all to yourself right on the water of Lake Eugenia in the Grey Highlands. This fully furnished 3-bedroom cottage is equipped with a brand-new kitchen, appliances, wood burning stove, furnace and water heater. You'll also have FREE access to unlimited WiFi, so you can work or stay in touch, when needed. Our cottage is suitable for a great get-away with any group, family or friends who are looking for a peaceful and enjoyable holiday from their busy lives.

Guest favourite
Cottage in Flesherton
4.95 out of 5 average rating, 40 reviews

Private Waterfront, Dock — Lake Eugenia Escape

Experience lake front views from Red Rooster Point Cottage on Lake Eugenia. Enjoy a fully equipped kitchen with cozy open concept living and dining area, comfortable sleeping quarters and large outdoor living spaces. The outdoor spaces include a large, elevated deck, full sun dock with swimming access (clean and no weeds) , cozy fire pit and hot tub. A short drive to a setting in paradise with the comforts of home (less than 2 hours from Toronto). Welcome!

Popular amenities for Flesherton holiday rentals

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  4. Grey County
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