Holiday rentals with a pool in Grey Highlands

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.

4.98 out of 5 average rating, 192 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 (closed for the winter season- to reopen Spring '26) *Tennis Courts *Ski or Hike In/Out to the North Hill (hiking trails, intermediate-advanced daytime skiing)

Chalet in Blue Mountain Resort Area

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, 302 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 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, 167 reviews

Blue Mountain Studio Retreat

Our cozy studio is located at the base of Blue Mountain at the North chair lift, with ski in / ski out access. Perfect for 2 or a couple with small children, this newly renovated Studio has 1 bedroom, 1 bathroom and sofa bed; fully stocked kitchen, electric fireplace and flat screen T.V. Only 1 km from the Village with many restaurants, shopping and activities. Enjoy a short trip to the Scandinavia Spa or many close by beaches. Blue Mountain is a great place for the whole family to enjoy.

4.96 out of 5 average rating, 141 reviews

Cottage in Tiny

Ultimate Georgian Bay Vacation Getaway

Come and stay at our beautifully renovated *all-season* beachfront cottage and enjoy a breathtaking panoramic view of Georgian Bay! You'll discover the cottage sitting atop a sand dune, right on one of the most stunning freshwater beaches in the world. This rare location hosts a private covered deck hovering over the white sand, in a beach house closer to the bay than anywhere else around! Summer guests also enjoy use of a heated salt water pool and large resort deck created by Paul Lafrance.

A spacious living area features tall windows allowing natural light to fill the room. A large screen TV is mounted above a gas fireplace, surrounded by comfortable seating. Decorative pillows enhance the sectional sofa, and an elegant coffee table sits centrally, adding to the inviting atmosphere.

4.96 out of 5 average rating, 228 reviews

Après Blue- 2bed2bath w/Pool 6 min walk to village

Welcome to Apres Blue at Blue Mountain! Unbeatable location @ 110 Fairway Court, only a 5 minute walk to Blue Mountain Village, Ski lifts & Monterra Golf Course. Professionally decorated ground floor unit with full kitchen, gas fireplace, high speed internet, walk out private patio with outdoor dining area, private gas BBQ and shared seasonal pool. This spacious ground floor, 2 bedroom, 2 full bathroom end unit townhouse has everything you need to enjoy your stay! License #LCSTR20230000084

4.92 out of 5 average rating, 117 reviews

Cottage in Meaford

Woodski Winter Haven: Mountain Cottage Near Skiing

This private mountain retreat is just 15 minutes from Blue Mountain, features 3.2 acres of beautiful scenery, a swimming pool and a renovated home for 10 guests (Max 8 adults). The house sits at the foot of a private 500ft mountain that is yours to explore all year around. Inside, there is a spacious home built for entertainment. Enjoy all-year fun at the property or head out to enjoy the amazing activities nearby. Only 5 minutes to the beach and 15 minutes to the best skiing in Ontario!

4.85 out of 5 average rating, 397 reviews

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

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.

An open concept living and dining area features a comfortable grey sectional sofa and two circular coffee tables on a textured area rug. The kitchen bar is equipped with four high-backed chairs. Large windows allow natural light to illuminate the space, with views of lush greenery outside.

4.94 out of 5 average rating, 540 reviews

3BR Sierra Scandi Chic - Closest to Village

Treat yourself to a getaway at our uncluttered, spacious, and fully-equipped 3 bedroom end-unit stacked townhouse at 110 Fairway Court. Just a 5 minute walk from the village and facing the Monterra golf course 1st hole, you’ll enjoy beautiful views of the mountain and easy access to village activities. With over 1,600 square feet of living space and all the comforts of home, our place has everything you need for a relaxing stay. Taxes include 13% HST and 4% municipal accommodation tax

A spacious open-concept living area is highlighted, featuring a large dining table set for meals. The kitchen is equipped with modern appliances and black cabinetry. Natural light enters through multiple windows, enhancing the inviting atmosphere of the space.

4.98 out of 5 average rating, 188 reviews

Lovely 3 Bedroom Condo with Stunning View and Pool

Beautifully Newly Renovated Condo Located in Rivergrass on Fairway Crt, which is in the heart of Blue Mountain and Steps to the Village! Condo features 3 bedrooms(One king, two Queen and Two Twin beds with trundle pullouts), 2 full baths, kitchen, washer/dryer, living room, and dining room. Outdoor Pool (Open from June 1 to Sept 20) and Hot Tub(All Year). Short walk or take the shuttle bus to the village. Our cleaners are extensively disinfecting and sanitizing between each booking.

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, 334 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 (closed for the winter season- to reopen Spring '26) *Tennis Courts *Ski or Hike In/Out to the North Hill (hiking trails, intermediate-advanced daytime skiing)

An open-concept studio unit is shown, featuring a cozy living area with a dark sectional sofa and a wooden coffee table. The king bed is visible in the background, accompanied by modern bedding. The kitchen area includes a bar with stools and is equipped with countertop appliances.

4.99 out of 5 average rating, 121 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 (closed for the winter season- to reopen Spring '26) *Tennis Courts *Ski or Hike In/Out to the North Hill (hiking trails, intermediate-advanced daytime skiing)!

Chalet in Blue Mountain Resort Area

The living area features a comfortable sofa adorned with cushions, positioned near a stone fireplace. Large windows allow natural light to fill the room, showcasing views of the surrounding greenery. A dining table with wooden chairs is visible, creating a cozy space for gatherings.

4.91 out of 5 average rating, 417 reviews

Immaculate Blue Mountains chalet

Welcome to our cozy chalet located in walking distance of Blue Mountain village. The chalet has been recently updated, including a luxurious king bed. Through winter, enjoy a relaxing evening by the fire, after a day on the slopes. In summer, enjoy time at the pool, after day on the golf course. The chalet is equipped with everything you need for a tranquil getaway. Enjoy free shuttle service to the village. STA Licence # LCSTR20220000127

Popular amenities for Grey Highlands rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A spacious bed is adorned with a textured white bedspread and a decorative 'welcome' pillow. Behind the bed, a scenic mural displays misty mountains and lush forests, enhancing the room's atmosphere. Two sleek reading lights are positioned on either side, adding functionality to the space.

4.84 out of 5 average rating, 108 reviews

Cozy Corner Townhome | Shuttle To The Village

4.89 out of 5 average rating, 253 reviews

Large 4 Br - 4.5 Bathroom: 2 King beds/Sauna/games

4.86 out of 5 average rating, 102 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 Shanty Bay

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

4.91 out of 5 average rating, 117 reviews

The entrance features double doors in a dark finish, adorned with elegant seasonal wreaths. Flanking the doors are decorative wall art pieces. A small bistro table with two chairs is positioned on a stone patio, complemented by potted snake plants and decorative pumpkins.

Home in Barrie

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

The living area features large windows allowing natural light to illuminate the space. A modern sectional sofa with colorful pillows and a decorative throw faces a sleek coffee table. A cozy fireplace is positioned beneath a wall-mounted TV, creating a warm environment.

4.88 out of 5 average rating, 128 reviews

Blue Mountain Retreat In Historic Snowbridge

A master bedroom features a spacious bed adorned with a blue and white comforter. Light wooden flooring is complemented by a decorative nightstand and a stylish chandelier. Large windows allow natural light to fill the room, offering views of the greenery outside.

4.94 out of 5 average rating, 219 reviews

Serene mountainside home with View/Shuttle Bus

4.89 out of 5 average rating, 159 reviews

A cozy bedroom features a spacious bed adorned with a white and blue floral duvet. Warm lighting is provided by bedside lamps on either side of the bed. A tasteful horse artwork is displayed on the wall, complementing the calming blue walls.

Home in Chatsworth

Stonehaven - large country retreat, with pool*

4.88 out of 5 average rating, 207 reviews

The kitchen features an open layout with warm wood flooring and a large dining table set for twelve. Natural light enters through two windows beside the door. Stainless steel appliances and a well-equipped countertop complete the functional space.

Home in Kimberley

Heart of Kimberley - with views and a hot tub

Apartment rentals with a pool

4.88 out of 5 average rating, 283 reviews

Aerial view of a charming multi-unit building surrounded by lush greenery. The structure features a combination of yellow and white exteriors, with distinct architectural details. A paved parking area is visible in the foreground, providing ample space for vehicles.

Apartment in Oro

Spacious 1-br w jacuzzi at Horseshoe Valley

The open concept living area features a spacious sofa with blue accent pillows, a flat-screen TV mounted above a modern fireplace, and large windows providing natural light. A dining area with bar stools is visible, complemented by a rustic wooden table.

4.82 out of 5 average rating, 209 reviews

Blue Escape | Ski-In-Out, Hot Tub & Shuttle

A cozy living area features a plush sectional couch and a wooden coffee table. Large windows provide views of the golf course, allowing natural light to brighten the space. A modern fireplace adds a welcoming touch, complemented by soft curtains and decorative wall accents.

4.93 out of 5 average rating, 573 reviews

*Blue Mountain Village* Pool, Hot Tub, WalkToBlue

An open-concept living area showcases a modern kitchen with stainless steel appliances and a large island. A cozy seating area features a dark sofa and an armchair, positioned near a stone fireplace. Natural light fills the space through multiple windows.

4.92 out of 5 average rating, 183 reviews

Blue Mountain condo in Historic Snowbridge

A modern kitchen area features blue cabinetry with open shelves displaying neatly arranged dishes. A central island with seating for two is complemented by sleek bar stools. Stainless steel appliances are integrated into the kitchen layout, providing a functional and inviting cooking space.

4.87 out of 5 average rating, 473 reviews

Base of Blue Mountain, Modern Studio

The open concept living area features a modern sofa and armchair arranged around a glass coffee table. A gas fireplace is centered on the wall beneath a mounted TV. Light streams through large windows, illuminating the space.

4.88 out of 5 average rating, 277 reviews

Hidden Haven - Shuttle to the Village & Ski lifts

A bright living area features large windows that allow natural light to fill the space. Comfortable seating is arranged around a central coffee table, with a modern fireplace and a wall-mounted TV providing amenities. Soft, neutral tones dominate the décor, creating a relaxed atmosphere.

4.97 out of 5 average rating, 110 reviews

3 Peaks at Blue Mountains, your luxury staycation!

The living room is designed with a cozy sectional sofa and a coffee table placed centrally. A mounted flat-screen TV is positioned above a white-brick fireplace. Natural light filters through sheer curtains, enhancing the welcoming feel of the space.

4.94 out of 5 average rating, 344 reviews

Cozy & Charming Retreat at Blue Mountain

Other holiday rentals with a pool

4.99 out of 5 average rating, 149 reviews

A spacious outdoor area features a picnic table and multiple lounge chairs arranged on well-maintained grass. The wooden structure in the background has large windows, adorned with awnings, and is surrounded by greenery under a clear blue sky.

Farm stay in Markdale

Experience Country Living at Firefly Ridge

Villa in Blue Mountain Resort Area

An outdoor space features a large rectangular swimming pool surrounded by a tiled patio. Lounge chairs with red cushions are positioned nearby. The modern house presents a mix of dark masonry and stone accents, set against a backdrop of lush greenery.

4.88 out of 5 average rating, 49 reviews

The Blue Mountains New Villa

Chalet in Blue Mountain Resort Area

A spacious living and dining area features a natural wood dining table set for six. The modern kitchen connects seamlessly with the open layout, while a comfortable seating arrangement faces a gas fireplace. Large windows provide ample natural light and views of the surrounding landscape.

4.98 out of 5 average rating, 121 reviews

Blue Mountain Escape! Lux 3 bdrm. Hot Tub!

An open-concept living and dining area features a large wooden table with gray chairs. A comfortable gray sofa and armchairs are arranged around a coffee table. Large windows offer views of the mountains, framed by yellow drapes, and a light fixture hangs above the dining table.

5 out of 5 average rating, 58 reviews

Gorgeous Two Bedroom Condo Overlooking Ski Hill

A spacious living room features large windows allowing natural light to fill the area. Comfortable sofas are arranged around a coffee table, complemented by a soft rug. A fireplace adds warmth, while a large television is mounted above the mantel.

4.99 out of 5 average rating, 150 reviews

Blue Mountain Escape! Pool&HotTub. Walk to Village

4.84 out of 5 average rating, 63 reviews

Home in Feversham

The Castle

4.84 out of 5 average rating, 105 reviews

The spacious living area features a comfortable couch and an additional patterned armchair. Two side tables with lamps are present, providing soft lighting. Large windows with sheer curtains allow natural light to fill the room, while a flat-screen TV is mounted on the wall.

Flat in Shanty Bay

Spacious Hideaway in Nature

Two cozy armchairs are presented, adorned with mountain-themed cushions. The backdrop features a rustic wooden wall with decorative ski equipment and a furry wall hanging, complemented by a small potted plant and a decorative orange object on a white table.