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House vacation rentals in Grey Highlands

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Top-rated house rentals in Grey Highlands

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A community heated outdoor swimming pool is surrounded by lush greenery and a variety of seating options, including blue umbrellas. The clear blue water reflects the sky, creating a serene setting for relaxation. Lounge chairs are positioned along the poolside for guest use.

Home in Blue Mountain Resort Area

4.89 out of 5 average rating, 240 reviews

Large 4 Br - 4.5 Bath; Sauna/Heated Pool/2 King

Heated Pool is currently Open. Imagine a super large, cozy vacation home nestled in the heart of Blue Mountain Ski Resort, offering a perfect blend of luxury and comfort. Four bedrooms with 2 King beds. This expansive retreat boasts multiple levels to provide the utmost relaxation and tranquility. The home features 4.5 spacious bathrooms. Our Sauna and Entertainment basement is ready for guests' enjoyment. Walk to the Village or take a Free Shuttle Bus. Walk to Pool in 1 minute from our home.

Top guest favorite

A cozy living area features a plush gray sofa and two bright armchairs, inviting relaxation. Natural light filters through the large windows, illuminating the wooden log walls and earthy decor elements, while a small coffee table sits in the center.

4.98 out of 5 average rating, 187 reviews

Log Cabin in the heart of downtown Elora

The Cabin Elora is a beautiful rustic log cabin stylishly updated with modern and hand made furniture from a local artisan. You will enjoy a clean, bright and open concept space. Located in the heart of Elora, walking out the door into downtown yet nestled off the street giving you wonderful privacy and a quiet peaceful atmosphere. Features: • King size bed with Egyptian cotton sheets • Private patio overlooking Metcalfe St. and gardens • Clean, stocked kitchen • Perfect downtown location

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

4.97 out of 5 average rating, 106 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

The exterior of the cottage showcases a welcoming covered front deck framed by vibrant greenery. A sturdy wooden staircase leads to glass doors. The space features modern outdoor seating with bright yellow accents, surrounded by well-maintained gravel and flower arrangements.

Home in Wiarton

4.99 out of 5 average rating, 117 reviews

Huckleberry’s Hideaway (Sauna, Starlink Internet)

Relax and enjoy the true cottage lifestyle with a clean, restful and modern feel. Perfect spot to enjoy a peaceful getaway warming up in the Sauna or around the fireplace. Centrally located on the Bruce Peninsula to Tobermory and Sauble Beach. Lovely views of Berford Lake with a public beach only 10 min drive away. Family friendly or couples getaway - we’ve got you covered. Cozy interior, with lots of parking, beautiful covered front decking. BBQ, campfires, Sauna you name it - it’s here.

Home in Badjeros

4.94 out of 5 average rating, 126 reviews

JJ’s small town country retreat

Take a step back in time to this old farm house. Located on the corner of our little town called Badjeros. This house was built in the 1930s and it’s been in our family for over 80 years. Since then there has been numerous upgrades to the house as well as a large 1200 square foot open concept addition built onto the existing house. While out in the country, this house is central to many attractions in the area 1.5 hours south of Toronto/GTA. Blue Mountain/ Collingwood is 30 minutes north.

Top guest favorite

The newly built cottage features a modern design with large windows reflecting the vibrant fall foliage. A spacious front patio is enhanced by seasonal plants in decorative pots. An inviting pathway leads to the entrance, surrounded by lush greenery.

Home in Wiarton

4.97 out of 5 average rating, 173 reviews

Kiss & Bond Water View Colpoys Bay 4 -Seasons

Hello,, I'm the owner of a newly built home, that I hope I will provide first-rate, memorable experiences for my guests, I'm a nurse for over 30 years, and I love to explore. Im an animals lover, I'm also a mother of 3 boys and have been married for 33 years ,being outdoors is one of my favourite activities, snowmobiling, hiking. I've owned our cottage for 10 years and we decided to rebuild , to enjoy the beautiful views of Colpoys Bay and in the back yard the Bruce Pennisula escarpment

The image captures a heated outdoor swimming pool with a gentle curve, surrounded by lounge chairs and blue umbrellas. The pool area is complemented by a well-maintained landscape, including shrubs and seasonal flowers. A clubhouse is visible in the background, providing nearby amenities.

Home in Blue Mountain Resort Area

4.94 out of 5 average rating, 209 reviews

Pool Open / Serene mountainside home View/Shuttle

Heated Pool currently Open! Welcome to this peaceful haven within the mountains. We have decorated our spacious and cozy home with comfortable beds, ample living amenities, and high-quality furniture to welcome you, your family and friends. Enjoy the carefully curated art pieces collected from around the world and look upon a stunning view of the snow-capped mountains from the master bedroom. Heated outdoor pool is seasonal! Walkable to the Village. Free Shuttle Bus

A serene outdoor swimming pool is surrounded by lush greenery and vibrant flowers. Several lounge chairs are arranged along the pool's edge, complemented by shaded umbrellas. The clear blue water reflects the sky, creating a tranquil setting for relaxation.

Home in Blue Mountain Resort Area

4.82 out of 5 average rating, 103 reviews

Heated Pool Open Newer House Sauna/amenities/walk

Modern 3 bedroom/3.5 bathroom Home with Newly Finished Basement! Get Romantic view of the Mountains in night from the Master Bedroom. Fully Equipped Kitchen, Laundry, Smart TVs, netflix, Updated bathrooms, Huge new Sauna. Games room has - Pool table, smart TV, ping pong table! Huge backyard with BBQ! Heated Outdoor Swimming Pool during summer season. Just few mins walk or Free Shuttle bus access to Blue Mountains Village. Heated Pool is now CLOSED for the season!

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 charming entrance is framed by an inviting covered porch, featuring decorative woodwork and a bright yellow door. Lush greenery surrounds the entryway, providing a serene and welcoming atmosphere. A stone path leads toward the door, enhancing the home's inviting character.

4.96 out of 5 average rating, 813 reviews

Elora Heritage House

Welcome to Elora Heritage House, where unforgettable experiences await in the heart of Elora. Built in the 19th century, our meticulously crafted home exemplifies quality and attention to detail. Discover carefully curated rooms with mid-century furniture, modern design, and a nostalgic ambiance. Nestled amidst serene trees, generous natural surroundings, world-class dining, and shops are just steps away. Embrace the essence of Elora at our cozy haven.

A well-lit living area features two comfortable gray sofas adorned with patterned throw pillows. Warm wooden floors complement the neutral wall tones. A staircase with wooden steps leads to the upper level, while large windows allow natural light to brighten the space.

Home in Williamsford

4.95 out of 5 average rating, 159 reviews

Williamsford Blacksmith Shop

Make some memories at the historic stone blacksmith shop built 1888. Located in Williamsford, Ontario. Conveniently located to the historic sites, waterfalls, the Bruce trail, rail trails for hiking and snowmobiling. Short 20 minute drive to Owen Sound. Sauble Beach 40 minutes. Tobermory drive 1 hr 1/2. Markdale 20 minutes. Enjoy the sites surrounding or a peaceful night by the campfire with campfire wood provided.

Top guest favorite

A charming farmhouse is set amidst a lush green lawn, surrounded by mature trees. A white fence complements the landscape. The building features a red door and light grey siding. Two dogs can be seen on the grass, adding a warm touch to the serene country setting.

Home in Grey Highlands

4.96 out of 5 average rating, 142 reviews

Newly Renovated! Charming Beaver Valley Farmhouse

Quintessential Ontario 4+ bedroom century old farmhouse sitting on three private acres, comfortably updated and perfect for a quiet country getaway. Minutes from Lake Eugenia, Bruce Trail hiking and Beaver Valley Ski Club. 30 minutes to Thornbury, Collingwood, and the Blue Mountain. Enjoy the Grey Highland outdoors and relax by the wood burning fire.

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Chalets

Adventure-ready homes with après-ski style

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Grey Highlands house rentals

Free parking on premises

Air conditioning

House rentals with a pool

An open-concept living area is displayed, featuring a gas fireplace with a mounted television above it. A spacious wooden coffee table is centered on a light-colored rug. The dining area, with a dark table and chairs, is visible in the background, complemented by a well-equipped kitchen.

Home in Blue Mountain Resort Area

4.89 out of 5 average rating, 95 reviews

Rivergrass Oasis: Steps to Blue Mountain Village!

A serene outdoor space features a sparkling pool surrounded by a mix of greenery, including a neatly trimmed tree and ornamental stones. A wooden fence provides privacy, while decorative white stones add a clean touch to the pool area.

4.91 out of 5 average rating, 109 reviews

Luxurious 4BDRM-King Bed-Barrie-near Snow Resorts

Home in Blue Mountain Resort Area

4.88 out of 5 average rating, 122 reviews

Blue Mountain Retreat In Historic Snowbridge

A spacious living area features a comfortable sectional sofa facing a stone fireplace. A dining table with chairs is positioned nearby. Large windows allow natural light to fill the space, offering views of the outdoor greenery. A subtle artwork of a deer adorns the wall.

Home in Blue Mountain Resort Area

4.83 out of 5 average rating, 12 reviews

Charming One Bedroom at Snowbridge

Home in Chatsworth

4.89 out of 5 average rating, 157 reviews

Stonehaven - large country retreat, with pool*

Home in Kimberley

4.88 out of 5 average rating, 205 reviews

Heart of Kimberley - with views and a hot tub

A modern living area features a comfortable sectional sofa and a sleek coffee table, with a fireplace and TV mounted on the wall. A spacious bedroom showcases a king-sized bed and contemporary decor. A private indoor sauna adds a unique wellness element to the condo.

Home in Innisfil

4.92 out of 5 average rating, 114 reviews

Sauna*King Bed*Fireplace*SmartTV

Top guest favorite

4.97 out of 5 average rating, 102 reviews

Stylish 3BR | Hot Tub • Firepit • Cozy Fall Escape

Weekly house rentals

An outdoor seating area features a sectional sofa with soft cushions and a fire table, providing warmth during cooler evenings. A dining table surrounded by chairs is positioned on a spacious deck. The view includes the serene waters of Georgian Bay against a colorful sunset sky.

Home in Meaford

4.9 out of 5 average rating, 10 reviews

Georgian Bay Waterfront - Northwoods Lodge

A modern living area showcases a sleek leather sofa adorned with decorative pillows. A wall-mounted television is placed above an electric fireplace, which adds a warm glow. Natural light fills the room, reflecting off the light hardwood floors, while a framed art piece adds visual interest.

Home in Collingwood

4.75 out of 5 average rating, 65 reviews

The 1883 Century Hotel Suite

A spacious lakefront cottage is framed by lush green trees, featuring a large wooden deck adorned with potted plants. The grassy lawn in front provides ample space for relaxation and activities, while the backdrop of forested land enhances the natural setting.

Home in Flesherton

4.95 out of 5 average rating, 39 reviews

Cottage Escape on Lake Eugenia

A bright living area features a cozy corner seating with natural light filtering through large windows. A simple round coffee table sits centrally on a textured area rug, while a record player is positioned nearby on a cart, enhancing a minimalist aesthetic.

Home in South Bruce Peninsula

4.95 out of 5 average rating, 80 reviews

Pine Villa-Mediterranean Cottage with Hot Tub

A charming lodge is surrounded by lush trees, featuring gray wooden siding and a stone pathway leading to the entrance. The structure includes a distinct chimney and a small utility shed beside it, creating a cozy, inviting outdoor setting.

Home in Singhampton

4.94 out of 5 average rating, 34 reviews

Blue Mountain Riverside Lodge | Hottub & Sauna

The entrance hall features a warm entryway with hardwood flooring and a polished staircase. Natural light floods in through a large glass door leading to the outdoor area. A console table and a welcoming sign add to the inviting atmosphere.

Home in Kimberley

4.97 out of 5 average rating, 38 reviews

Paradise in the Valley

A spacious screened-in sunroom is filled with natural light, featuring large windows that offer views of the lush greenery outside. Comfortable sofas provide ample seating, while a coffee table and decorative elements create a relaxed atmosphere for enjoying the serene landscape.

Home in Kimberley

4.95 out of 5 average rating, 37 reviews

Hillside Haven Retreat: Sunroom & Pond Escape

A modern living area features a sectional sofa alongside two armchairs, designed with a neutral colour palette. A sleek coffee table sits in the center, while a wall-mounted smart TV is positioned above a linear fireplace. Natural light enters through a nearby window.

5 out of 5 average rating, 10 reviews

Entire Unit 2 bdr 2 bathroom | Full privacy

Private house rentals

The exterior of the home features a wrap-around deck with a black railing, complemented by outdoor seating. Stone and wood siding are visible, with lush greenery and colorful flowers surrounding the entrance. Large windows allow for bright natural light, enhancing the airy appearance.

Home in Meaford

4.9 out of 5 average rating, 68 reviews

Georgian Escape.Steps to Georgian Bay w/ hot tub

Top guest favorite

An open game room features a polished wooden pool table at its center, surrounded by exposed timber beams and vibrant green walls. Large windows provide natural light, while a television is mounted nearby. Additional seating is available, enhancing the space's social atmosphere.

Home in Meaford

4.98 out of 5 average rating, 93 reviews

Birdsong, the perfect Blue Mountains getaway

Top guest favorite

The cottage features a brick exterior with a ramp leading to the front door, making it accessible. Surrounding greenery complements the structure, while colorful flowers add a touch of vibrancy. A clouded sky and autumn foliage in the background enhance the natural setting.

Home in Mount Forest

4.96 out of 5 average rating, 53 reviews

Maple Forest Country Cottage

The exterior of a spacious country house is shown at dusk, featuring a blend of dark siding and stone accents. A large driveway leads to a two-car garage, while surrounding greenery and an open lawn provide a sense of privacy and tranquility.

Home in Singhampton

4.87 out of 5 average rating, 46 reviews

5+ bdr Cottage Collingwood Blue Mountain Singhamp

The cottage exterior is illuminated at dusk, showcasing its modern design. Large windows reveal the open-concept interior, while a spacious deck offers seating options. The surrounding landscape features a manicured lawn and trees in the background, enhancing the serene lakeside setting.

Home in Orillia

4.7 out of 5 average rating, 10 reviews

[Casa Luna]Chic Lakehouse| BBQ|HotTub|LakeViews

Top guest favorite

The exterior of the cottage is showcased, featuring a modern gray siding and large windows. A welcoming red front door is framed by a well-maintained garden with green foliage and blooming white flowers, creating a pleasant entrance.

5 out of 5 average rating, 77 reviews

River's Edge Retreat

Top guest favorite

The large bedroom features a queen canopy bed with detailed linens. A decorative rug in warm tones complements the wooden furniture. Natural light filters through the window blinds, and a chair is situated in one corner, adding comfort to the space.

Home in Midland

5 out of 5 average rating, 88 reviews

Historic Coach House hosted by John & Donna

Top guest favorite

A charming brick house sits on a well-maintained lot, surrounded by lush greenery and tall trees. The front yard features manicured grass and a small tree, while a paved driveway leads to a two-car garage on the side.

Home in Wasaga Beach

5 out of 5 average rating, 31 reviews

Dream Retreat: Relaxing Vacation

Quick stats about house rentals in Grey Highlands

Total rentals
260 properties
Total number of reviews
7.3K reviews
Family-friendly rentals
230 properties are a good fit for families
Pet-friendly rentals
110 properties allow pets
Rentals with a pool
60 properties have a pool
Rentals with dedicated workspaces
150 properties have a dedicated workspace

Destinations to explore