Vacation rentals in Lily Oak

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Top-rated vacation rentals in Lily Oak

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Top guest favorite

The exterior of a charming tiny house is showcased, featuring a rustic wooden design and a welcoming deck. Large windows allow for ample natural light, while a pergola extends over part of the deck, creating a shaded area for outdoor relaxation amidst a lush, green landscape.

Tiny home in Kimberley

4.98 out of 5 average rating, 166 reviews

Hand-Crafted Cabin in Stunning Beaver Valley

Lovingly designed and built tiny house in the heart of the beautiful Beaver Valley. 2 Double beds, small kitchenette, rustic deck & living area with a gorgeous outhouse. The property has extensive edible landscapes & greenhouse filled with seedless grapes & edible perennials. Beautiful views of the escarpment, close to the Bruce Trail & Beaver River access point for canoeing and kayaking. Shop at the achingly charming Kimberley General Store. Close to Blue Mountains, Thornbury & Collingwood

Guest favorite

A cozy loft bedroom features a spacious bed dressed in soft white and blue linens. Light wood flooring complements the blue and dark walls, while bedside tables with lamps provide gentle illumination. A plush robe hangs nearby, and a small rack holds towels for convenience.

Guest suite in Chatsworth

4.86 out of 5 average rating, 389 reviews

Settler's Loft in Log Home

This charming original log home is set amongst rock fences and mature maples on 80 acres of reforested farmland. This two-storey suite sleeps up to 5 guests, has 2 bedrooms, 4-piece bathroom, kitchenette, living area, deck, & private balcony. Trails for exploring, campfire ring, and large grassy area for outdoor games. Brand new AC system. Very close to OFSC snowmobile trails. (Note - barn access is for weddings only) NO pets >> 40 minute drive to Blue Mountain; 30 minutes to Lake Huron beaches

Top guest favorite

A spacious glamping tent is set on a wooden platform surrounded by trees. The tent features an open entrance and is complemented by outdoor seating with two blue chairs. Natural light illuminates the interior, creating a welcoming environment.

Yurt in Holland Centre

4.99 out of 5 average rating, 145 reviews

Greyridge Glamping "Paradise Island " Retreat

Grey Ridge Glamping "Paradise island" is a unique small island surrounded by clear running water from our beautiful stream. There are winding paths & bridges that lead to tent. Featuring a King Size bed, seasonal propane heater, wing-back chairs ,solar lighting and cell phone chg. station. Outdoor washroom facilities in its own enclosed structure. As well an “open to the sky” cedar lined hot water shower. Cooking station with wash and Prep areas. Perfectly suited for a couples private getaway!

Top guest favorite

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

4.98 out of 5 average rating, 127 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 favorite

Two glasses of rosé wine sit on a decorative table, capturing sunlight against a backdrop of rolling hills. The landscape features vibrant autumn foliage in shades of orange and yellow, with a clear blue sky and wispy clouds visible above.

Place to stay in Chatsworth

5 out of 5 average rating, 117 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.

Top guest favorite

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, 153 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.

Superhost

An aerial view of the tiny house surrounded by lush greenery and trees. The rustic wooden structure features a slanted red roof and an inviting porch area with seating. A clear view of the grassy land leads to the house, emphasizing its quaint and natural setting.

Tiny home in Meaford

4.85 out of 5 average rating, 378 reviews

Tiny Home Nestled between Thornbury & Meaford

Tinyhome situated 10 min to Thornbury and Meaford, and 20 min from Blue Mountain Village, nestled a country/residential area so it is quiet and dark at night. Has all the basic comforts including spacious 3 piece bathroom. Close drive to beaches and many hikes and cross country ski trails in the area. It is also a 15 minute drive from Beaver Valley Ski Club and a number of different cideries. Shared heated pool available for the summer months. Window Aircon/pool opens end of May or June.

Top guest favorite

A serene outdoor space features four wooden chairs arranged around a fire pit on lush green grass. Behind, two vibrant autumn trees stand beside a tranquil lake, framed by a white fence and scenic hills in the background.

Guest suite in Kimberley

4.96 out of 5 average rating, 243 reviews

"Wine Down" in Scenic Grey Highlands

Join us at “Wine Down”, our beautiful property located on the highlands of the Beaver River Valley, just minutes away from all that Georgian Bay and the Blue Mountains have to offer. It is a very private 1 acre property with an incredible view of water, escarpment and wildlife. Enjoy more than 1,000 sq. ft. of living space including beds for 5, fully equipped kitchen, dining area, living room with large screen TV and full bathroom. Your hosts live on sight in the main level of the house.

Guest favorite

A wooden deck connects two buildings, featuring outdoor furniture including two lounge chairs and a blue plastic chair. A picnic table is positioned in front, and a grill can be seen nearby. Lush greenery surrounds the area, providing a calm outdoor environment.

Chalet in Grey Highlands

4.95 out of 5 average rating, 143 reviews

Private 5 Acre Chalet with Bunkie & Sauna

An enchanting, private, 4 season retreat in the escarpment atop Beaver Valley, metres from a beautiful section of the Bruce Trail. The property has nearly 5 acres with cut trails, hammocks, and a sports field. It has two buildings connected by a large deck that has outdoor furniture and a BBQ. The sauna is just feet away. The buildings are fully outfitted offering a comfortable base for daily adventuring, or a stay put retreat. This spot is ideal for a family, or a couple's getaway.

Top guest favorite

An outdoor space features a picnic table with an umbrella, set near a tranquil pond. A stack of firewood is positioned beside a large tree, with a fire pit nearby. Lush greenery surrounds the area, creating a peaceful atmosphere.

Guesthouse in Southgate

4.92 out of 5 average rating, 205 reviews

Cozy, quiet, clean cabin with wi-fi and fire pit.

Welcome to Penny Creek. A simple cabin just south of Durham. A private location surrounded by ponds, streams and forest - yet close to many day adventures should you want to explore beyond the property. Nearby amenities include restaurants, grocery, lcbo, fuel, coffee and shopping . An open concept space that offers one queen bed and a pull out sofa. Full kitchen and bath. Picnic tables, Fire pit and bbq. Excellent hiking trails nearby. Easy access to ofsc (snowmobile) trails!

Guest favorite

An outdoor balcony area is presented with comfortable seating arranged around a wooden table. Soft lighting is strung above, illuminating the space. Lush greenery provides privacy and a tranquil atmosphere, while a few lounge chairs are positioned for relaxation.

Home in Grey County

4.95 out of 5 average rating, 162 reviews

The Post Office Motel Boutique

Where luxury and style meet relaxation! The Post Office Motel is a boutique experience with all the luxuries of a day at the spa in peacefully designed space intended to send you straight into vacation mode. Step out of your car and right into the cutest hidden gem of a town known as Kimberley. Located steps to TWO undeniable restaurants, run by top chefs; Justin’s Oven & Hearts Tavern. Georgian Trail at your door step, 20 min to Blue Mtn, 15 min to Thornbury

Top guest favorite

A cozy living room features a teal sofa, a brown armchair, and a wooden television stand. A flat-screen TV is mounted on the wall. A patterned area rug covers the hardwood floor, while a coffee table with a geometric design sits in the center. Natural light enters through a window.

Apartment in Owen Sound

4.96 out of 5 average rating, 151 reviews

Suite on the Creek

Keep it simple at this peaceful and centrally located walkout apartment. The suite backs onto the Niagara escarpment and sections of the Bruce Trail. Though you’ll feel secluded in nature, head out front and you can walk downtown in less than 15 minutes. Rest well in the king-sized bed that looks out onto the walking bridge in the back yard. Enjoy cozy evenings in with a movie and a fire, or relax with a book in your private backyard sitting area.