Ski-in/Ski-out holiday rentals in Grey Highlands

A cozy family room features a spacious gray sectional sofa and a wooden coffee table. Light-colored walls and a patterned rug create a welcoming atmosphere. In the background, a kitchen area is visible, equipped with modern appliances and seating for two.

4.93 out of 5 average rating, 326 reviews

Cozy Studio Mountainside stay in Blue Mountains

Enjoy spring or summer in Blue Mountains! Book your much getaway now. This cozy ground-floor STUDIO condo is perfect for a couple or girls getaway(max 4). Features a comfy queen bed, pop-up sofa bed, full bathroom, electric fireplace, and full kitchen with everything you need. Free parking included. The hot tub is open daily. Pool opens in May. Access to Blue Mountain hiking trails and activities. Blue Mountain Village is only a 5-minute drive (20-minute walk) with great restaurants and shops.

An open layout of the studio unit is displayed, featuring a modern kitchen with a breakfast bar and sleek cabinetry. The cozy living area contains a pullout sofa with decorative cushions, and a spacious king bed is situated in the corner, complemented by subtle green accent walls.

4.97 out of 5 average rating, 232 reviews

Evergreen Studio-KingBed/Pool/HotTub/Shuttle

Renovated studio unit at the North Creek Resort featuring: * King Bed * SMART TV, High-Speed Rogers Ignite WIFI and TV * Pull Out Sofa * Stone Fireplace * Modern, Stylish Decor *please note there is not a traditional oven- there is a microwave/convection oven combo along with a stove top *Shuttle Service *Year Round Hot Tub *Pool (Scheduled to open Fri May 15 2026- Tues Oct 13 2026) *Tennis Courts *Ski or Hike In/Out to the North Hill (hiking trails, intermediate-advanced daytime skiing)

4.9 out of 5 average rating, 125 reviews

A cabin is nestled among a lush forest, surrounded by an expanse of green trees. The landscape features varying shades of foliage, with the cabin partially visible from above against the backdrop of the vibrant forest canopy.

Cabin in Paisley

Secluded 4 bed cabin on a river w/ 85-acres.

Cabin on a hill along the Saugeen River beside 700 acres of trails. SKI-IN/OUT or Snowplow cost split 50/50 between guest/host NEW washroom and deck! This is a family cabin. Not a destination for parties. STARGAZERS: Zero pollution SNOMOBILE trails next door! HIKERS: public trails Brant Tract FISHING: On the Saugeen HUNTERS: 85 acres of Sugarbush. Must declare prior. 6 guests max! Camera in the driveway. More than 6 people are billed as a separate cost, DOUBLING the cost of your booking

Chalet in Blue Mountain Resort Area

The exterior of the chalet features a two-story structure with large windows providing ample natural light. A small balcony is visible above the lower level, accompanied by a natural gas BBQ. Colorful adirondack chairs in red and blue are placed on the patio, surrounded by green shrubbery.

4.91 out of 5 average rating, 462 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

Townhouse in Blue Mountain Resort Area

An entertainment area is showcased, featuring a pool table with various colored balls scattered on its surface. A TV is mounted on the wall opposite a comfortable sofa, which is adorned with colorful cushions. Soft lighting enhances the inviting atmosphere.

4.92 out of 5 average rating, 108 reviews

New Cozy home walk Village/Shuttle Bus/ Pool Table

Beautifully decorated for comfort and cozy. Our vacation home would like to welcome you and your group. Your whole group will enjoy everything our home has to offer including a finished basement with entertainment games such as Pool table, Foosball table, more sitting area and an extra full bathroom as well. Our Kitchen is fully stocked. We have 4 comfortable beds, 2 Sofa beds and 4.5 bathrooms to share. Walk to the Blue Mountain Village is only 7 minutes or take a free shuttle bus.

An open-concept living area features a spacious bed with a dark headboard and matching bedside lamps. A modern kitchen is visible, highlighted by stainless steel appliances and a breakfast bar with three stools. A soft gray couch with decorative pillows is placed in the foreground.

4.89 out of 5 average rating, 111 reviews

Studio Condo @ North Creek|Pool/Hot Tub/Crave TV

Come and relax by the mountain and enjoy our renovated open concept living space. Our clean & comfortable studio condo has everything you need for a memorable getaway. We want you to have a fantastic time and have stocked our condo with all the things we expect when we travel. You'll find all the extras that make a place special: 40 inch flat screen T.V., fresh linens, well stocked kitchen, newer furnishings & decor, napoleon fireplace, deep jetted tub & free WiFi, NETFLIX and cable.

Cottage in Grey Highlands

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.

4.95 out of 5 average rating, 156 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.

Place to stay in Blue Mountain Resort Area

A bright and open living area features large windows overlooking the deck. A wall-mounted flat-screen television is positioned above a floating shelf. A cozy armchair with a red cushion complements the gray sofa, while light wood flooring adds warmth to the space.

4.84 out of 5 average rating, 627 reviews

Close to Village, 2 Bed Loft Condo.

Our chalet is an updated, clean 2-bed/2-bath chalet at the base of Blue Mountain, ideal for a winter getaway. Enjoy true ski-in/ski-out convenience with the North Ski Lift just 150m away. Our unit is unique within the resort, offering a private main-floor bedroom that adds comfort and flexibility after long days on the slopes. With the Village, Scandinavian Spa, cafés and restaurants only 1km away, it’s the perfect home base for skiing, snowshoeing and cozy après-ski nights

The studio features a spacious living area with a comfortable sofa and a modern armchair. A king bed adorned with blue and yellow linens is positioned in the background. Natural light filters through the window treatments, enhancing the serene ambiance.

4.84 out of 5 average rating, 458 reviews

Ski in/out @ North Creek W King bed! New Hot Tub

Welcome to our beautiful studio at the foot of Blue Mountain ski hills. Fully renovated from top to bottom in 2021 and ready for visitors! 'Cascade Cabin' is a modern studio which sleeps 3 and features a King bed with a queen sofa bed in the living area. Unit features a fully equipped kitchen with seating for 3, full bathroom with shower & new soaker tub. The condo is located within minutes from Blue Mountain Village and within walking distance to the north ski lift.

The airy studio unit features a spacious king bed framed by green accent walls. A cozy sectional sofa is positioned in front of a coffee table. Natural light filters through window shutters, highlighting the adjacent balcony with Muskoka chairs.

4.96 out of 5 average rating, 381 reviews

Studio at Blue-KingBed/Pool/HotTub/Shuttle

Welcome to our studio unit in the mountainside North Creek Resort! *King bed *sofa bed-double sized memory foam mattress *SMART TV, High-Speed Rogers Ignite WIFI and TV *Cookware, Utensils and Keurig *freshly painted *remodeled washroom Property Features: *Shuttle Service *Year Round Hot Tub *Pool (Scheduled to open Fri May 15 2026- Tues Oct 13 2026) *Tennis Courts *Ski or Hike In/Out to the North Hill (hiking trails, intermediate-advanced daytime skiing)

4.87 out of 5 average rating, 305 reviews

Stylish & Spacious 2 Bdrm/2 bths/2 balc Condo Loft

STA Licence - LCSTR20240000021 Welcome to our Stylish and Spacious 2 bedroom, 2 bathroom, 2 balcony & 2 level condo loft. Located at the foot of the north hills at Blue Mountain with ski-to-slope access and stunning views of the hills and just a short walk away to Blue Mountain Village. It will comfortably sleep 4, with room for 6 with 1 sofa bed. Linens, towels and toiletries are available as well as unlimited wifi. Complimentary parking is available.

4.98 out of 5 average rating, 182 reviews

Alpine Bliss: King Bed/Pool/HotTub/Shuttle

Newly renovated studio unit at the mountainside North Creek Resort featuring: * King Bed * SMART TV, High-Speed Rogers Ignite WIFI and TV * Double Pull Out Sofa * Remodeled Washroom *Equipped Kitchen with Keurig * Modern, Stylish Decor *Shuttle Service *Year Round Hot Tub *Pool (Scheduled to open Fri May 15 2026- Tues Oct 13 2026) *Tennis Courts *Ski or Hike In/Out to the North Hill (hiking trails, intermediate-advanced daytime skiing)!

Popular amenities for Grey Highlands ski-in/ski-out rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Ski-in/ski-out house rentals

Home in Blue Mountain Resort Area

5 out of 5 average rating, 13 reviews

Peak Perfection @ The Blue Mountains

4.93 out of 5 average rating, 192 reviews

A cozy living area features an orange L-shaped sofa adorned with decorative pillows, paired with a round coffee table. A 55" smart TV sits on a sleek black stand against the wall, surrounded by neutral decor and natural light from the nearby window.

Home in Barrie

4 Bedroom Fully Private Townhouse in Barrie

4.86 out of 5 average rating, 115 reviews

A bright and spacious living area features a comfortable white sofa paired with dark blue accent chairs. A stylish dining table is set for meals, while a gas fireplace and mounted television create a cozy atmosphere. Natural light fills the room through large windows.

Home in Horseshoe Valley

King Bed, Pool, Gym, Ravine View, Your Getaway!

Home in Blue Mountain Resort Area

The exterior of the town-home is showcased, featuring a combination of stone and blue siding. Neatly manicured lawns surround the property, and several large windows allow natural light to illuminate the interior. A small tree is planted in the foreground, adding a touch of greenery.

4.85 out of 5 average rating, 119 reviews

Blue Mountain Village Townhome 4 Bedroom w Shuttle

4.97 out of 5 average rating, 139 reviews

An open and airy space features a large harvest table with pink legs, complemented by wooden chairs. A cozy bench is positioned alongside the table. A staircase leads to a loft area, while art supplies and decor are visible throughout the room.

Home in Desboro

Forest Loft - Forest, Sauna, Ponds & Stargazing

4.7 out of 5 average rating, 128 reviews

A modern bathroom is equipped with a walk-in shower featuring marble-like tiles. A wall-mounted mirror reflects soft light from three globe fixtures above a large sink, complemented by grey cabinetry. Two neatly hung towels are visible, and a small rug adds warmth to the floor.

Home in Brampton

Brand new One Bedroom apartment

4.95 out of 5 average rating, 143 reviews

Home in Collingwood

Driftwood on 6th Heritage Downtown Collingwood

Home in Blue Mountain Resort Area

A spacious living area features high vaulted ceilings and a stone-accented fireplace. Large windows allow natural light to brighten the space, highlighting plush furnishings arranged for relaxation. A television is mounted above the fireplace, complementing the warm, inviting decor.

4.74 out of 5 average rating, 57 reviews

Ski/Golf 3 Bedroom Chalet Condo/Mountain Views

Family-friendly, ski-in/ski-out home rentals

4.8 out of 5 average rating, 218 reviews

Blue Escape | Modern Stay + Hot Tub & Shuttle

A modern dining area features a large wooden table surrounded by six upholstered chairs. Above, a geometric light fixture provides illumination, while artwork hangs on the wall, complementing the warm tones of the cabinetry visible in the kitchen.

4.89 out of 5 average rating, 204 reviews

Close to Village, 2 Bedrooms , Rivergrass

5 out of 5 average rating, 79 reviews

A charming A-frame cabin stands amidst tall grass, with the sun setting in the background. The metal roof glistens softly under the warm light, while large windows reflect the serene surroundings. Wildflowers can be seen in the foreground, adding natural beauty to the scene.

Guesthouse in Meaford

From A to Zen - a refined glamp

Loft in Blue Mountain Resort Area

A bright and airy living area features a comfortable sofa and an armchair positioned near a large flat-screen television. Natural light floods the space through multiple windows, leading to a private deck with mountain views.

4.87 out of 5 average rating, 119 reviews

Pool & Hot Tub 2 Bedroom, 2 floor home

A cozy living space features a flat-screen TV mounted on the wall above a wooden media console. There are two small tables in front of a comfortable grey sofa, with a light neutral rug underneath. The kitchen area is visible, showcasing modern appliances and bar stools.

4.81 out of 5 average rating, 190 reviews

TIMBUK-BLUE Ski In/Ski Out

4.86 out of 5 average rating, 65 reviews

A dining area features a long wooden table surrounded by six chairs, with vibrant red cushions. A vase is placed at the center of the table, and sunlight streams through a large window, illuminating the room and offering a view of the greenery outside.

Cottage in Oro Station

Farmhouse next to Bike, Hike, Ski Forest Trails

Chalet in Blue Mountain Resort Area

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

A cozy sleeping area is highlighted by a black wooden bed frame with a crisp white bedding set. Decorative pillows are arranged on the bed, while a framed image of a bear adorns the wall. Soft bedside lighting is provided by sconces, complementing the mirror opposite.

4.9 out of 5 average rating, 191 reviews

Blue Mountain Studio Retreat

Ski-in/ski-out condo rentals

4.91 out of 5 average rating, 100 reviews

An aerial view captures the expansive layout of Friday Harbour, showcasing various buildings along the marina and natural surroundings. A peaceful golf course is visible with a distinctive lighthouse, all framed by serene water reflections under a twilight sky.

Condo in Innisfil

Family-friendly luxury getaway at Friday Harbour

4.93 out of 5 average rating, 91 reviews

Condo in Innisfil

Luxury Getaway | Friday Harbour Condo

A modern living area is highlighted by a sleek gas fireplace, surrounded by a light-colored sectional sofa. A low-set coffee table sits in the center, complemented by hardwood flooring that enhances the spacious layout. A flatscreen TV is mounted on the wall across from the seating.

4.9 out of 5 average rating, 252 reviews

Hillside Hideaway | Patio Views + Walk to Village

Condo in Horseshoe Valley

A spacious studio features a king-size bed with premium bedding, adjacent to a stylish sectional couch. Natural light pours in through large windows, illuminating the open floor plan. A dining table is positioned nearby, providing a comfortable area for meals.

4.68 out of 5 average rating, 76 reviews

Lux Studio in Horseshoe Valley

A modern living area is featured, showcasing a grey sofa and two armchairs. A coffee table sits in front of the seating arrangement, and a wall-mounted television is positioned above a linear fireplace. Natural light streams through large windows, illuminating the space.

4.93 out of 5 average rating, 403 reviews

2 Bedroom, 2 Level Condo on Blue Mountain!

Condo in Horseshoe Valley

A spacious bedroom is highlighted by a king-size bed with a plush white comforter. Two round mirrors adorn the black accent wall, reflecting natural light from the window. A soft tan throw blanket and decorative pillows complement the bed, alongside a bedside table and a green potted plant.

5 out of 5 average rating, 5 reviews

Luxurious King Bed Jacuzzi Condo–Pool, Gym, Sauna

Condo in Horseshoe Valley

The bedroom displays a king-sized bed adorned with soft linens and multiple decorative pillows. Next to the bed, a stylish lamp provides warm light, while three framed nature photos hang above the headboard. A cozy seating area features a plush sofa with decorative cushions and a small table, enhancing comfort.

4.98 out of 5 average rating, 53 reviews

Serenity 1Bed+Sauna+HotTub+Indoor/OutdoorPool

A comfortably furnished living area features a brown sofa positioned in front of a mounted flat-screen television. A modern electric fireplace is located beneath the TV, adding warmth to the space. Natural light filters through light-colored drapes and shuttered windows.