Vacation rentals with a pool in Grey Highlands

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Grey Highlands

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favourite
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.
Dome in Bradford West Gwillimbury
4.96 out of 5 average rating, 419 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...

Guest favourite
A peaceful beach scene captures the soft sand shoreline leading to the water's edge. Gentle waves lap at the shore, and the sky is filled with warm sunset hues. A cottage is visible in the background, nestled among trees, enhancing the serene atmosphere.
Cottage in Tiny
4.96 out of 5 average rating, 139 reviews

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.

Guest favourite
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 homes in Meaford
4.85 out of 5 average rating, 396 reviews

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.

Top guest favourite
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.
Condo in Blue Mountain Resort Area
4.98 out of 5 average rating, 183 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.

Top guest favourite
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.
Apartment in Blue Mountain Resort Area
4.99 out of 5 average rating, 186 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 * New Pull Out Sofa * Stone Fireplace * Modern, Stylish Decor *please note there is not a traditional oven- there is a microwave/convectional oven combo along with a stove top *Shuttle Service *2 Year Round Hot Tubs *Pool *Tennis Courts *Ski or Hike In/Out to the North Hill (hiking trails, intermediate-advanced daytime skiing)

Guest favourite
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
4.92 out of 5 average rating, 413 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

Guest favourite
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.
Condo in Blue Mountain Resort Area
4.93 out of 5 average rating, 568 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.

Top guest favourite
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.
Apartment in Blue Mountain Resort Area
4.96 out of 5 average rating, 329 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 *2 Year Round Hot Tubs *Pool *Tennis Courts *Ski or Hike In/Out to the North Hill (hiking trails, intermediate-advanced daytime skiing)

Top guest favourite
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.
Apartment in Blue Mountain Resort Area
5 out of 5 average rating, 111 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 *2 Year Round Hot Tubs *Pool *Tennis Courts *Ski or Hike In/Out to the North Hill (hiking trails, intermediate-advanced daytime skiing)!

Superhost
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.
Condo in Blue Mountain Resort Area
4.9 out of 5 average rating, 559 reviews

Blue Mountain Studio with Summer Pool

Ground floor unit, ideal for couples. Ski in-ski out. Blue Mountain village nearby. Complex with tennis courts & outdoor seasonal pool. Modern & chic unit - renovated in 2019. New appliances, barn-wood wall accent, bathroom vanity, furniture. Under 500sq ft with kitchen, Netflix, WIFI, Queen bed, sofa pull out, en-suite bath & jet tub. Your very own sanctuary space. North Creek Rentals HOA.

Guest favourite
The open concept living area features a comfortable sofa, accent chairs, and a flat-screen TV positioned near a fireplace. Light enters through large windows adorned with sheer curtains, while a cozy area rug anchors the space. A well-equipped kitchen island with bar seating enhances the functionality.
Loft in Blue Mountain Resort Area
4.8 out of 5 average rating, 314 reviews

Stay A While • Ski-In/Out • Hot Tub & Shuttle

Stay A While Chalet is located in North Creek Resort at the North Base of Blue Mountain just steps from the ski hills and hiking trails, and minutes from Blue Mountain Village. Enjoy resort perks including a free shuttle, year-round hot tub, tennis courts, BBQs, and picnic areas. The outdoor pool is open for a fall/winter trial but may close at any time without notice.

Guest favourite
The living area features a comfortable gray sofa with decorative pillows and a light gray accent chair. A wooden coffee table holds small decor items, while natural light enters through multiple window panes with white blinds. A soft area rug adds warmth to the space.
Loft in Blue Mountain Resort Area
4.88 out of 5 average rating, 241 reviews

Mountainside Escape – Ski-In/Out • Pool • Shuttle

Mountainside Escape is located in North Creek Resort at the North Base of Blue Mountain just steps from the ski hills and hiking trails, and minutes from Blue Mountain Village. Enjoy resort perks including a free shuttle, year-round hot tub, tennis courts, BBQs, and picnic areas. The outdoor pool is open for a fall/winter trial but may close at any time without notice.

Popular amenities for Grey Highlands rentals with a pool

When is the best time to visit Grey Highlands?

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Avg. price$201 CAD$212 CAD$188 CAD$155 CAD$163 CAD$176 CAD$211 CAD$218 CAD$151 CAD$176 CAD$151 CAD$220 CAD
Avg. temp-7 °C-6 °C-1 °C6 °C12 °C17 °C20 °C19 °C15 °C9 °C3 °C-3 °C

Quick stats about vacation rentals with a pool in Grey Highlands

  • Total vacation rentals

    Explore 490 vacation rentals in Grey Highlands

  • Nightly prices starting at

    Grey Highlands vacation rentals start at $56 CAD per night before taxes and fees

  • Verified guest reviews

    Over 45,070 verified reviews to help you choose

  • Family-friendly vacation rentals

    350 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 150 rentals that welcome pets

  • Rentals with dedicated workspaces

    300 properties have a dedicated workspace

  • Wifi availability

    490 of Grey Highlands vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Grey Highlands rentals

  • 4.8 Average rating

    Grey Highlands stays are highly rated by guests—averaging 4.8 out of 5!

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