Chalet holiday rentals in Grey Highlands

An open concept living space features a pool table at the center, surrounded by a sectional couch and a small dining table. Large windows provide natural light, while a 70-inch TV is mounted on the wall. A gas fireplace is visible in the background.

4.97 out of 5 average rating, 202 reviews

Entire Rustic Chalet - Hot Tub, Sauna, Large Yard!

This updated chalet in the heart of Blue Mountain surrounded by forest includes a huge front yard, balcony, hottub, sauna, pool table, darts, foosball and is only a 3min drive to the BM Village. The great room has an amazing Polk audio surround sound with 70"4k TV ideal for movie nights after a long day skiing. 5 of the 7 bedrooms have there own 32"TVs for more private entertainment before bed. The mattresses are very comfy for a quality sleep so you will be well rested for the next day of fun.

A bright bedroom features a spacious bed covered with soft linens and a textured throw. The walls are painted blue, complemented by decorative curtains. A piece of artwork depicting a deer is displayed above the bed, and a bedside lamp is positioned on a small white table.

4.97 out of 5 average rating, 318 reviews

The Little Blue Spruce! Free shuttle to village

Welcome to The Little Blue Spruce Chalet, the place to unwind and rejuvenate. Located 5min from the village, this spacious unit comes with everything you might need to make your vacation carefree: fast internet, cable and multiple streaming channels, lots of linens and towels, a washer/dryer and a fully stocked kitchen. Relax on the back patio watching the birds and bunnies, walk 2 min to the pool or take the free shuttle to the village. Message me for more info! LICENCE NO. LCSTR20220000080

A spacious living area features comfortable black leather seating arranged around a central wooden coffee table. A gas fireplace is set against a stone wall, while large windows allow natural light to fill the room, showcasing views of the surrounding landscape.

4.98 out of 5 average rating, 131 reviews

Blue Mountain Escape! Lux 3 bdrm. Hot Tub!

STA License #LCSTR20220000018 Fabulous 3 bedroom 2 bath executive suite with premium features, is an upper level end unit townhome located next to the Village at Blue Mountain in the beautiful Rivergrass community. Walk to Monterra Golf Clubhouse and Conference Centre. Steps to the Village featuring award winning restaurants/bars, shops, ski/snowboard hills, mini-golf, biking, hiking, zip lining +. A short drive from the GTA, Blue Mountain is a wonderful year round playground for all ages.

4.91 out of 5 average rating, 488 reviews

An open concept living area features high ceilings and ample natural light from large full-length windows. A comfortable seating arrangement is positioned around a fireplace, with a television and a dining area visible nearby, creating a welcoming space for relaxation.

Chalet in Priceville

Hilltop Chalet | Hot Tub, Fireplace & Sunrise View

ReLive Retreat's four-season chalet in Ontario. The Hilltop Chalet is a cozy 700 sq ft open-concept cabin set high on the land with beautiful sunrise views. Enjoy a private hot tub, indoor fireplace, firepit, full-length windows, wrap-around deck, BBQ, filtered spring water, and access to hiking trails. Ideal for couples or friends seeking rest, comfort, and nature immersion. Friendly-dog-friendly by request. Located on a private 72-acre retreat with shared trails, cabins, and on-site owners.

4.82 out of 5 average rating, 122 reviews

Chalet in Flesherton

The Red House – Private Wooded Oasis & Hot Tub

Unplug in our private 3-acre forest retreat. Wake up in a king bed, brew coffee in the fully-stocked kitchen, then step onto the wrap-around deck surrounded by cedar forest. After hiking the Bruce Trail, skiing at Beaver or Blue, paddling Lake Eugenia or enjoying a foodie-road-tour, sink into the sparkling hot tub. Evenings end around the wood stove or the outdoor fire-pit under a star-filled sky. Fast Wi-Fi, cozy beds and thoughtful touches make every stay easy, relaxing and memory-filled.

An exterior view of a row of chalet-style condominiums is presented, showcased under a blanket of snow. Large windows reflect the surrounding winter landscape, while the ocean can be seen in the background. The scene conveys a tranquil, snowy atmosphere.

4.91 out of 5 average rating, 443 reviews

Modern Ski In/Out Mountain Side Ground Floor

SKI IN AND SKI OUT from the back deck (snow dependent)!! Notice the amount of comfortable seating for NINE PEOPLE around the TV that many other places are without. At the end of a long ski day having a comfortable place for everyone to sit is what most Chalets are missing. Enjoy our family’s beautiful renovated GROUND FLOOR chalet with 2 Bedrooms, 2 Baths, 6 Beds conveniently located next to the Blue Mountain Inn. Blue Mountain Village is a 7 minute walk away. Location, Location, Location

A spacious living area is highlighted by modern furnishings, including two dark sofas and a wooden coffee table. A kitchen island with bar seating offers additional space, while dining chairs surround a large table in the background. Bright lights illuminate the well-equipped kitchen and open layout.

4.97 out of 5 average rating, 183 reviews

King’s Escape at Blue Mountain

Welcome to our cozy, ground-level, two-bedroom condo in Historic Snowbridge, just a short walk from Blue Mountain Village-your perfect year-round escape! Backing onto Monterra Golf Course, you’ll enjoy stunning views and endless outdoor activities. Ski in winter or hike and bike in summer. Relax at our *seasonal* outdoor pool and take advantage of free rides to the village. Amenities include comfortable sleeping for families, a fully equipped kitchen, and a cozy living space LCSTR20210000165

A welcoming living area is highlighted by a soft gray sofa and a comfortable light-colored couch adorned with cushions. A coffee table sits atop a vibrant area rug. Large glass doors provide a view of the outdoor space, while a stone fireplace adds warmth to the room.

4.91 out of 5 average rating, 225 reviews

Cosy Chalet - 4 Season Family Oasis

Welcome to Snowbridge chalet, our sunny, 4-season private retreat. Professionally designed and decorated, the chalet is the perfect getaway for families, only a 10 minute walk or 3 minute drive to all the ski & snowboarding activities and fun of Blue Mountain village. With room enough for 6 guests, our 2 bed, 2 bathroom ground level chalet backs onto Monterra golf course, providing lots of space for outdoor time and bbq's. Includes all the comforts of home for the perfect relaxing escape.

4.98 out of 5 average rating, 115 reviews

Chalet in Meaford

Sundance of Blantyre Ski Lodge w/ Hot Tub & Sauna

Welcome to Sundance of Blantyre! Step back in time in this historic yet modernized Lodge! This 3600 sq. ft retreat on the Bruce Trail has Breathtaking Valley Views from your own Private Hot Tub & Fire Pit all the Way to Georgian Bay. We invite you to enjoy our truly unique and tranquil getaway with 6 bedrooms + Private Sauna House! With 3 firepits, swimmable/fishing pond, hiking, cross country skiing and snow shoeing + snowmobile/ ATV trail access at your door, Your adventure awaits!

4.95 out of 5 average rating, 155 reviews

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

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.

A modern chalet exterior is highlighted by a gray facade and multiple windows, allowing natural light to enhance the space. Lush greenery surrounds the entryway, providing a welcoming environment. The neatly paved parking area complements the structured landscaping, inviting guests to explore the comfort within.

4.8 out of 5 average rating, 372 reviews

Cozy Sleep 10 ,Hot Tub & BBQ, Steps to Blue Mtn

You just found the perfect Blue Mountain getaway! Our cozy 2,500 sqft chalet is ideal for friends and families seeking to relax and recharge. A 5-minute walk from the village and just 400 yards from the ski lifts, it sleeps 10 comfortably. Enjoy an indoor hot tub, a game room with foosball, TV, and Pac-Man, plus a gourmet kitchen and wood-burning fireplace for cozy nights in. Grill on the Weber BBQ or unwind in the loft. Have questions? Message us anytime—we’re here to help!

4.95 out of 5 average rating, 502 reviews

Chalet in Coldwater

OakRidge Retreat-HOT TUB 100s of acres WIFI

The cottage provides a serene space to share with fiends and family surrounded by nature. Enjoy beaver ponds along the trails, indoor/outdoor games, wood burning stove, sauna, hot tub, firepit, wifi, jetted tub 75" & 55" smart tv's and streaming services. Fully equipped kitchen, double oven, granite counter. In winter, snowshoes and snow saucers. At Christmas the house is decorated and boasts a 15 ft tree. 20-25 minutes from Mount St. Louis ski hill and several beaches.

Popular amenities for Grey Highlands chalet rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly chalet rentals

A spacious sleeping area features a dark wood bed frame with a light-colored duvet and decorative pillows. Two bedside lamps provide soft lighting. A large wardrobe with sliding doors is visible in the background, and the warm wooden flooring complements the neutral color palette.

4.82 out of 5 average rating, 874 reviews

Blue Mountain / Collingwood Hill Side Condo

An inviting dining area features a large wooden table adorned with a decorative centerpiece. The fully-equipped kitchen, visible in the background, showcases modern appliances and sleek cabinetry. Ample natural light enters through nearby windows, enhancing the room's welcoming ambiance.

4.98 out of 5 average rating, 85 reviews

2 Lake/Ski chalet with HOT TUB/SAUNA

Superhost

A layer of snow covers evergreen branches, creating a serene winter scene. The snow accumulates delicately on the needles and surrounding foliage, highlighting the texture of the branches against the dark earth below.

4.78 out of 5 average rating, 110 reviews

Retreat at Blue with private Hot Tub

4.79 out of 5 average rating, 53 reviews

The exterior of a Victorian farmhouse is displayed, featuring a metal roof and rustic wooden siding. A spacious deck is visible, surrounded by vibrant flower beds and green lawn. Seating areas include patio furniture and a fire pit, offering a welcoming outdoor space.

Chalet in Mulmur

The Sheds: Victorian Farmhouse 5BR Ski-In Ski-Out

4.93 out of 5 average rating, 201 reviews

A bright dining area features a wooden table surrounded by chairs. Large windows offer views of the lush exterior landscape. A woven light fixture hangs from the ceiling, and a bench is placed against the wall, enhancing the natural ambiance.

Chalet in Sauble Beach

STUNNING Post & Beam Retreat: Short Walk to Beach!

4.91 out of 5 average rating, 77 reviews

Chalet in Meaford

UrbanChalet: Secluded 20Acres W/Pizza Oven+Firepit

Superhost

An open concept kitchen and dining area is displayed, featuring a large wooden table with benches. Bright light floods the space through floor-to-ceiling windows, offering views of the surrounding greenery. A fully equipped kitchen is visible in the background with modern appliances.

4.65 out of 5 average rating, 130 reviews

Large Blue Mountain Chalet Near Village Sleeps 20

4.94 out of 5 average rating, 267 reviews

Chalet in Gravenhurst

Log Cabin on the Lake Bed and Breakfast

Luxury chalet rentals

A sunlit living area showcases a soft seating arrangement, complemented by a wooden coffee table. A decorative chair and a gas fireplace with flames create a cozy ambiance. A staircase, leading to the upper level, is visible in the background. A large TV is mounted on the wall.

4.86 out of 5 average rating, 22 reviews

The Cottages at Blue - Cottage 2

An inviting living area displays high ceilings with wooden paneling. Comfortable seating arrangements are oriented around a central coffee table. A modern fireplace is situated against a feature wall, and large windows allow natural light to fill the space, enhancing the atmosphere.

4.81 out of 5 average rating, 208 reviews

Chalet At Blue - Private chalet with hot tub

A uniquely shaped chalet is framed by a snowy landscape, featuring a spacious wooden deck that wraps around the front. Large windows allow natural light to fill the interior, while a clear blue sky complements the winter scenery.

4.83 out of 5 average rating, 181 reviews

Octagon Chalet fire pit, close to theVillage

4.91 out of 5 average rating, 58 reviews

The cottage exterior is highlighted by warm lighting that enhances its modern design. Large windows provide views of the surrounding greenery, while a spacious deck, adorned with string lights, complements the tranquil setting. The scene conveys a welcoming atmosphere for outdoor gatherings.

Chalet in Collingwood

*NEW* Naturskön Cottage | Mountain Views | Hot Tub

A modern chalet with a multi-level facade is set amidst trees and shrubbery. The entrance features a large, bright door flanked by windows. A porch with a shaded seating area is visible, surrounded by well-maintained landscaping and stone accents.

4.98 out of 5 average rating, 115 reviews

Walk to the village at Blue - Regal

Superhost

A spacious dining area features a large wooden table with bench seating under an arched ceiling. Large windows allow for natural light, highlighting the rustic stone accents and wooden beams. A cozy seating area is visible in the background, enhancing the inviting feel of the space.

4.89 out of 5 average rating, 120 reviews

Rustic Spanish Chalet inthe Heart of Nature/hottub

A private hot tub is set in a serene outdoor space, surrounded by greenery. Two blue chairs are positioned on a tiled surface, leading to a striped mat that guides the way to the hot tub. Towering trees provide a natural backdrop.

4.88 out of 5 average rating, 51 reviews

Lake/Ski chalet with HOT TUB/SAUNA

5 out of 5 average rating, 53 reviews

A log home nestled among tall trees in a snowy landscape captures the essence of winter. The structure features large windows, allowing natural light to flood the interior, and stone pathways guide the way through the serene outdoor space.

Chalet in Mulmur

Into the Woods Log Home

Lakefront chalet rentals

4.9 out of 5 average rating, 71 reviews

Two dark blue adirondack chairs are positioned beside a fire pit on a gravel area overlooking the tranquil water of Brewster's Lake. Lush greenery and trees line the opposite shore, complementing the peaceful outdoor setting.

Chalet in Singhampton

3 Bedroom Lakefront Cottage on secluded lake.

The exterior of the villa is shown, featuring a two-story structure with a light-colored facade and a prominent arch above the entrance. Lush greenery frames the entryway, and a pathway leads to the front door. The water of Georgian Bay is visible in the background.

4.89 out of 5 average rating, 18 reviews

The Aqua Villa

4.97 out of 5 average rating, 30 reviews

A serene outdoor space features Muskoka chairs arranged around a fire pit on a lush green lawn, framed by trees. The tranquil waters of Colpoy's Bay are visible in the background, along with a dock and Canadian flags gently waving by the shore.

Chalet in Wiarton

TGIF - Serene Waterfront Retreat