Vacation rentals with a pool in Grey Highlands

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, 424 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...

Apartment in Blue Mountain Resort Area

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, 190 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, 301 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

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.

Townhouse in Blue Mountain Resort Area

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, 227 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

4.85 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.

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, 187 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 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, 276 reviews

Hidden Haven - Shuttle to the Village & Ski lifts

Hidden Haven is located in the peaceful Historic Snowbridge community. Snowbridge is just a 2-minute drive, a 20-minute walk, or a quick shuttle ride from the heart of Blue Mountain Village, where you will find the ski hills, restaurants, shops, and more. The community offers a complimentary shuttle service to Blue Mountain Village, an outdoor swimming pool available during the summer months, and scenic walking trails with views of Blue Mountain for guests to enjoy during their stay.

A bright kitchen and dining area feature a modern white countertop with seating, complemented by a wooden table surrounded by dining chairs. Natural light enters through several windows, and a clock adorns the wall, enhancing the space's functionality and warmth.

4.96 out of 5 average rating, 164 reviews

Rustic Chic Renovated 2Bd Condo by Village

**Welcome to your ideal all-season retreat!** This beautifully renovated 2-bedroom ground-level unit is thoughtfully designed to offer all the comforts of home, complete with modern upgrades. Perfect for up to 6 guests, this charming chalet provides the perfect balance of comfort and convenience—just a 3-minute drive or an 12-minute walk from Blue Mountain. Whether you're here for adventure or relaxation, this is the perfect place to stay year-round. STA License # LCSTR20230000022

Apartment in Blue Mountain Resort Area

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.

5 out of 5 average rating, 118 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)!

Superhost

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.

Chalet in Blue Mountain Resort Area

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

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, 571 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 closed for the season.

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, 107 reviews

Cozy Corner Townhome | Shuttle To The Village

Superhost

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, 101 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, 218 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

Condo rentals with a pool

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, 182 reviews

Blue Mountain condo in Historic Snowbridge

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.

4.88 out of 5 average rating, 187 reviews

Close to Village, 2 Bedrooms , Rivergrass

4.83 out of 5 average rating, 138 reviews

The living area features a comfortable sofa beside a stone fireplace, providing a cozy focal point. A light-toned armchair sits nearby, while a television is mounted on the wall. Natural light enters through the glass door, leading to an outdoor space.

Condo in Oro

Cozy 1-Bedroom Romantic Retreat with full Kitchen

4.87 out of 5 average rating, 280 reviews

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

A spacious living area features a modern fireplace with a stone surround and a wall-mounted flat-screen TV. A small blue chair complements the neutral tones, while the open kitchen includes a breakfast bar with two high stools. Natural light enters through the window, illuminating the room.

4.85 out of 5 average rating, 112 reviews

BLUE MOUNTAIN STUDIO OASIS

The open-concept living area features two comfortable sofas with decorative cushions. A dining table is set for six nearby, while kitchen access is visible in the background. Natural light enters from large windows, with wooden accents enhancing the space.

4.87 out of 5 average rating, 146 reviews

Out of the Blue | Shuttle to Village & Ski lifts

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.

4.92 out of 5 average rating, 381 reviews

2 Bedroom, 2 Level Condo on Blue Mountain!

Superhost

A modern living area features a cozy futon with decorative cushions, complemented by a wooden coffee table. Sunlight filters through the window with white blinds, illuminating the space. A dining table for four is visible, and a doorway leads to the separate bedroom.

4.8 out of 5 average rating, 245 reviews

Mountainside Retreat - Ski in/out - Endless Coffee

Other vacation rentals with a pool

4.95 out of 5 average rating, 296 reviews

A wooden dining area features a round table surrounded by four wooden chairs. The kitchen showcases wooden cabinets, a stove, a microwave, and a refrigerator. Natural light enters through a window above the sink, enhancing the warm wood tones of the room.

Cottage in Wasaga Beach

GATED RESORT COTTAGE

Guest suite in Orangeville

This inviting bedroom features a spacious bed adorned with soft linens and a textured throw. A large armoire stands alongside, complemented by decorative plants and soft lighting. Natural light is welcomed through an adjacent glass door leading to a private entrance.

4.92 out of 5 average rating, 818 reviews

HotTub & Cozy Fireplace - Headwaters Retreat

4.95 out of 5 average rating, 330 reviews

A charming two-story cabin is nestled among lush greenery, with a pathway leading to the entrance. Tall trees and well-maintained hedges surround the home, creating a sense of privacy. Soft sunlight illuminates the cabin, enhancing its rustic appeal.

Cabin in Mono

The Trails Retreat (Private Cabin)

4.9 out of 5 average rating, 243 reviews

A loft area features a wooden railing adorned with greenery, providing a cozy viewing spot. A circular wooden table is accompanied by two matching folding chairs, inviting relaxation. Warm lighting enhances the natural wood tones of the ceiling and walls, creating a welcoming ambiance.

Cottage in Alcona

Utopia villa and spa

Apartment in Blue Mountain Resort Area

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

Townhouse in Blue Mountain Resort Area

A dining area features a wooden table set with a red-striped runner and natural decorations. In the background, the kitchen is visible, showcasing modern appliances and cabinetry. The living space is bright and welcoming, adorned with comfortable seating, including a grey couch and decorative accents.

4.96 out of 5 average rating, 342 reviews

Great kitchen, comfy beds, games, walk 2 village +

5 out of 5 average rating, 14 reviews

A cozy living area features a light-colored leather sofa set with two cushions and a rustic wooden side table. Warm wooden paneling adds to the inviting atmosphere, while soft lighting enhances the comfort. A flat-screen TV is mounted on the wall, and adjacent rooms are visible.

Cottage in Flesherton

Waterfront Cottage #2