Holiday 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.

%{current} / %{total}1 / 1
Top Guest favourite
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.
Chalet in Blue Mountain Resort Area
4.97 out of 5 average rating, 318 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

Top Guest favourite
A spacious living area is highlighted by modern furnishings, including two dark sofas and a wooden coffee table. A kitchen island with bar seating offers additional space, while dining chairs surround a large table in the background. Bright lights illuminate the well-equipped kitchen and open layout.
Chalet in Blue Mountain Resort Area
4.97 out of 5 average rating, 183 reviews

King’s Escape at Blue Mountain

Welcome to our cozy, ground-level, two-bedroom condo in Historic Snowbridge, just a short walk from Blue Mountain Village-your perfect year-round escape! Backing onto Monterra Golf Course, you’ll enjoy stunning views and endless outdoor activities. Ski in winter or hike and bike in summer. Relax at our *seasonal* outdoor pool and take advantage of free rides to the village. Amenities include comfortable sleeping for families, a fully equipped kitchen, and a cozy living space LCSTR20210000165

Superhost
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.
Condo in Blue Mountain Resort Area
4.83 out of 5 average rating, 289 reviews

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

Relax and enjoy the beauty of the Blue Mountains nestled in this gorgeous two bedroom condo located directly across from the Blue Mountain Village in the prestigious Snowbridge community. - 10 minute walk to the Village - located on Monterra Golf Course - private backyard - the pool is shared with the residents of the subdivision (summer only) - BBQ - sleeps 6 comfortably - 5 min to town, stores/ amenities -condo is on the main floor level -pool open for summer only (May to September)

Superhost
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
4.86 out of 5 average rating, 409 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
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.
Townhouse in Blue Mountain Resort Area
4.94 out of 5 average rating, 550 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

Guest favourite
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.
Condo in Blue Mountain Resort Area
4.95 out of 5 average rating, 170 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

Top Guest favourite
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.
Condo in Blue Mountain Resort Area
4.97 out of 5 average rating, 114 reviews

3 Peaks at Blue Mountains, your luxury staycation!

A luxurious staycation, two-bedroom, two-bathroom ground floor condo. Enjoy the Blue Mountains year-round with a view of the ski hills and the 17th hole of the Monterra Golf Course. Our welcoming unit is a quick walk to the Blue Mountain Resort, short drives to world-class spas in the area, and steps away from fantastic outdoor activities available year-round. We have enjoyed the area for many years and will be happy to pass along our tips to make your stay wonderful!

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, 353 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)

Top Guest favourite
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
4.99 out of 5 average rating, 149 reviews

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.

Guest favourite
Home in Blue Mountain Resort Area
4.88 out of 5 average rating, 117 reviews

Rivergrass Oasis Across from Blue Mtn Hot Tub!

Rivergrass Oasis is located in the Beautiful Rivergrass community adjacent to Blue Mountain. This unit backs onto Monterra Golf Course, the community swimming pool and hot tub. This unit is within a 5-7 minute walk to the heart of Blue Mountain Village and Monterra Golf Course. Making this property an ideal location for those that want to park their car and walk to the all amenities at Blue Mountain such the ski hills, restaurants, shops, and activities.

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
4.91 out of 5 average rating, 425 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
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.
Condo in Blue Mountain Resort Area
4.94 out of 5 average rating, 357 reviews

Cozy & Charming Retreat at Blue Mountain

Enjoy a stylish experience at this centrally located retreat! Welcome to Rivergrass Resort with stunning views of beautiful Blue Mountain and backing onto the picturesque 18th hole of the award winning Monterra Golf Course. Our recently upgraded unit includes all the comforts of home with a modern flare. Short Term Accommodation License #LCSTR20210000237

Popular amenities for Grey Highlands rentals with a pool

When is the best time to visit Grey Highlands?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$202 AUD$213 AUD$190 AUD$156 AUD$164 AUD$177 AUD$212 AUD$219 AUD$152 AUD$164 AUD$159 AUD$242 AUD
Avg. temp-7°C-6°C-1°C6°C12°C17°C20°C19°C15°C9°C3°C-3°C

Quick stats about holiday rentals with a pool in Grey Highlands

  • Total holiday rentals

    Explore 480 holiday rentals in Grey Highlands

  • Nightly prices starting at

    Grey Highlands holiday rentals start at $70 AUD per night before taxes and fees

  • Verified guest reviews

    Over 45,560 verified reviews to help you choose

  • Family-friendly holiday rentals

    350 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 150 rentals that welcome pets

  • Rentals with dedicated workspaces

    290 properties have a dedicated workspace

  • Wi-Fi availability

    480 of Grey Highlands holiday rentals include Wi-Fi 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!

Destinations to explore

  1. Airbnb
  2. Canada
  3. Ontario
  4. Grey County
  5. Grey Highlands
  6. Rentals with pools