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.

4.96 out of 5 average rating, 228 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)

Dome in Bradford West Gwillimbury

Vibrant autumn foliage displays shades of yellow and orange surrounding a geodesic dome. A pathway of stone steps leads through a lawn covered in colorful leaves, creating a serene outdoor setting amidst lush greenery.

4.96 out of 5 average rating, 476 reviews

Four season glamping dome under the stars

Whether you are looking for a romantic getaway for two, a solo remote work week in solitude surrounded by nature, or a family adventure, this 4-season geodesic dome is just the right place. Explore picturesque trails of Scanlon Creek Conservation Area, enjoy inground pool in summer, experience breathtaking sunsets over the farm fields, the starry skies by the bonfire, mesmerizing dance of fireflies in June, and let the frogs and crickets lull you to sleep in the place where time stands still...

A clear, inviting outdoor pool is surrounded by landscaped greenery and stone seating areas. The pool features a curved shape with steps leading in, and two poolside lounge chairs are visible. Mature trees provide shade in the background, enhancing the serene environment.

4.96 out of 5 average rating, 358 reviews

Walk 2 Village, Great Kitchen & Beds, Summer Pool!

You will love our renovated condo with quality mattresses, well stocked kitchen, great bathrooms, on demand hot water & walk out rear patio with BBQ and yard access. Heated outdoor pool in complex July/Aug Trust our 350+ reviews telling stories of amazing stays & memories made! The short 5 minute stroll to the village is something you will be sure to enjoy! NETFLIX, cable & unlimited WIFI, cozy gas fireplace, quality towels/ linens + games/ Legos...message us with any questions or to book now.

Guesthouse in Orangeville

An outdoor pool area features a surrounding deck with wooden steps leading up to it. Bright blue water reflects the sky, and vibrant green grass borders the patio. Two red Adirondack chairs are placed nearby, complemented by lush trees and a distant green landscape.

4.96 out of 5 average rating, 385 reviews

Sunny Pines Farm Studio Tennis Court/Bruce Trail

Perfect for a getaway in the country. A bright, spacious, open-concept designer studio featuring beautiful rolling-hill vistas, queen bed, 3-piece bathroom, dedicated bbq, heat/AC plus a wood burning stove, wet bar with a Nespresso machine, deluxe counter-top oven & bar fridge and all new tennis court, laundry available upon request. Mono Cliffs, Boyne Valley, Hockley Valley Nature Reserve Prov. Parks & Mansfield Recreation Centre are minutes away. Ideal hiking, cycling, snowshoeing and xcsking.

4.86 out of 5 average rating, 428 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.

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.

4.99 out of 5 average rating, 212 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 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, 379 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)

4.99 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

Your private living space is comfortable and bright, with lots of picturesque windows and high ceilings. There is a walkout to a private area where you can relax, and unwind, enjoying the sounds of nature and some farm animals, such as horses, minis, donkeys, goats, chickens, cats, 2 Australian cattle dogs and even some piggies. We love our animals and we welcome yours as we are a pet friendly farm. PLEASE NOTE DOGS MUST BE ON A LEASH WHILE ON THE PROPERTY.

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, 623 reviews

*Blue Mountain Village* Pool, Hot Tub, WalkToBlue

SHUTTLE, HOT TUB & SEASONAL POOL 360 degree views! We are a 3-5 minute walk to the Village with stunning views of the golf course and mountain! Perfect place to relax on the balcony or couch after a busy day of soaking up all Blue has to offer! ★Self-Check In ★Equipped kitchen, towels & linens ★ SMART TV, WIFI & CABLE ★ Games, high chair, PackNPlay ★ Resort hot tub with indoor changeroom and washrooms ★ Pool expected to open the week of June 1 2026

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.

4.98 out of 5 average rating, 180 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)!

The bright living area features a modern design with a dark sectional sofa, accent chairs, and a round coffee table. Large windows provide views of snow-covered landscapes, while a gas fireplace adds warmth to the space. Decorative elements include potted plants and wall art.

4.93 out of 5 average rating, 202 reviews

View to Blue | Modern Escape • Walk to Village

Short walk to Blue Mountain for skiing! View to Blue is located in the beautiful Sierra Lane community adjacent to Blue Mountain. Just a 7-minute walk to the heart of Blue Mountain Village, you’ll have easy access to the ski hills, restaurants, shops, and more. The living room is the star, thoughtfully styled with warm décor and inviting touches that create a cozy, upscale space—perfect for relaxing after a day on the mountain.

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, 116 reviews

Cozy Corner Townhome | Shuttle + Patio + Pool

4.86 out of 5 average rating, 275 reviews

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

4.86 out of 5 average rating, 114 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!

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, 141 reviews

Blue Mtn Retreat w Summer Pool, XBox, Free Shuttle

4.92 out of 5 average rating, 132 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

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, 237 reviews

Serene mountainside home with View/Shuttle Bus

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

4.9 out of 5 average rating, 162 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*

Condo rentals with a pool

4.98 out of 5 average rating, 103 reviews

Condo in Innisfil

Stunning 1BR w Pool ~ Free Parking & Self Check-In

An open-concept living area features a large sectional sofa and a coffee table centered on a textured rug. A cozy fireplace is flanked by windows, allowing natural light to fill the space. Decorative wall paddles add a subtle touch of charm.

4.92 out of 5 average rating, 146 reviews

The Fairway Chalet

A bright living room is displayed with a gas fireplace and comfortable seating arranged around a circular coffee table. Large windows allow natural light to fill the space, while a cozy area rug adds texture. Decorative wall art enhances the inviting ambiance.

4.81 out of 5 average rating, 127 reviews

Clearview Chalet • Modern 3BR • Mountain Stay

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.

4.87 out of 5 average rating, 290 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, 116 reviews

3 Peaks at Blue Mountains, your luxury staycation!

A modern kitchen area is showcased featuring sleek white cabinetry and stainless steel appliances. A stone countertop provides space for meal preparation, complemented by four red stools. A bowl of green apples adds a fresh touch to the dining area, enhancing the inviting ambiance.

4.89 out of 5 average rating, 579 reviews

Blue Mountain Studio with Summer Pool

A spacious bedroom features a large bed with a light floral-patterned coverlet. Two bedside tables with lamps are positioned on either side, while soft light filters through a window adorned with light curtains. A framed artwork hangs above the bed, contributing to a calming atmosphere.

4.83 out of 5 average rating, 301 reviews

Private Backyard/Shuttle/Pool/10min walk 2 village

A light-filled living area features large windows with wooden blinds, allowing natural light to illuminate the space. A comfortable seating arrangement with a neutral palette surrounds a wooden coffee table, while a gas fireplace is positioned against a brick wall, providing a cozy focal point.

4.96 out of 5 average rating, 176 reviews

Rivergrass Retreat * Blue Mnt Village & Monterra *

Other holiday rentals with a pool

Two comfortable sofas with decorative pillows are positioned around a dark coffee table in a spacious living area. A minimalist art piece adorns one wall, while a staircase leads to the upper level. The modern kitchen is visible in the background.

4.89 out of 5 average rating, 178 reviews

The Snowbridge Lookout on Monterra Golf Course

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, 253 reviews

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

Chalet in Blue Mountain Resort Area

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, 226 reviews

Cosy Chalet - 4 Season Family Oasis

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.

4.99 out of 5 average rating, 134 reviews

Blue Mountain Escape! Lux 3 bdrm. Hot Tub!

4.9 out of 5 average rating, 267 reviews

A large inflatable duck with headphones floats in a swimming pool, surrounded by evening lighting. A covered seating area features string lights, enhancing the tranquil and fun atmosphere. The backdrop includes a well-lit house surrounded by greenery, creating a relaxing outdoor space.

Cottage in Alcona

Utopia villa and spa

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.

4.96 out of 5 average rating, 167 reviews

Blue Mountain Escape! Pool&HotTub. Walk to Village

4.99 out of 5 average rating, 214 reviews

Townhouse in Port Severn

Pool, Wifi, Free parking, Golf, Laundry, BBQ

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.