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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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Loft in The Blue Mountains

4.79 out of 5 average rating, 196 reviews

Stay A While Chalet - Outdoor Pool / 2 Patios

Stay A While Chalet is 2 bedroom loft located in North Creek Resort at the North Base of Blue Mountain. Ideal location for those seeking easy access to the ski hills and hiking trails but still within minutes to Blue Mountain Village. North Creek resort offers a free shuttle service to Blue Mountain Village, an outdoor swimming pool open in the summer months, two hot tubs year round, tennis courts with night lights, charcoal grills and community picnic tables that you can use during your stay.

May 22 – 29

G$22,605 GYD per night

Dome in Bradford West Gwillimbury

4.98 out of 5 average rating, 215 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...

Oct 22 – 29

G$25,063 GYD per night

Loft in The Blue Mountains

4.92 out of 5 average rating, 156 reviews

Mountainside Escape - Outdoor Pool / Hiking Trails

Mountainside Escape is a family friendly loft located in North Creek Resort at the North Base of Blue Mountain. Ideal location for those seeking easy access to the ski hills and hiking trails but still within minutes to Blue Mountain. North Creek resort offers on demand shuttle service to Blue Mountain Village, an outdoor swimming pool open in the summer months, two hot tubs year round, tennis courts with night lights, charcoal grills and community picnic tables that you can use during your st

Jun 7 – 14

G$31,296 GYD per night

Condo in The Blue Mountains

4.92 out of 5 average rating, 246 reviews

Cozy Studio Mountainside stay in Blue Mountains

Summer and Spring are the perfect time to visit Blue. This cozy STUDIO ground floor condo is perfect for a couple or small family (Max 4). The unit includes: a comfy queen bed and a pop up sofa bed, bathroom with jacuzzi tub, electric fireplace and full kitchen with everything you need. Free parking. Two shared hot tubs (open daily) and tennis courts. Easy access to for hiking trails. Pool opens in May. The Blue Village is only a 5 minute drive away with great restaurants and shops.

Sep 6 – 13

G$27,854 GYD per night

Farm stay in Essa

4.99 out of 5 average rating, 119 reviews

The Schoolhouse

Kick back and relax in this calm, stylish space. This school portable turned into a modern guest home is situated on acreage boasting with gorgeous views of forests, fields, grazing animals and sunsets. In warmer months, cool off in the stock tank pool, play on the volleyball court, and enjoy meals on the deck accessed from the bedroom and main entry. Relax by the campfire, walk nearby trails, visit restaurants, markets and shops. Planning your wedding? Ask about our wedding package!

Aug 24 – 31

G$36,827 GYD per night

Condo in The Blue Mountains

4.88 out of 5 average rating, 199 reviews

1 Bed, 1 Bath Lovely Open Concept Resort Condo

Come and relax by the mountain and enjoy our renovated open concept living space. Our clean & comfortable studio condo has everything you need for a memorable getaway. We want you to have a fantastic time and have stocked our condo with all the things we expect when we travel. You'll find all the extras that make a place special: 40 inch flat screen T.V., fresh linens, well stocked kitchen, newer furnishings & decor, napoleon fireplace, deep jetted tub & free WiFi, NETFLIX and cable.

Jun 14 – 21

G$28,087 GYD per night

Tiny home in Meaford

4.85 out of 5 average rating, 257 reviews

Tiny Home Nestled between Thornbury & Meaford

Tiny home situation 10 min to Thornbury and 10 min to Meaford, and 20 min from Blue Mountain Village, nestled a country/residential area. 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 pool available for the summer months with possibilities of covid restrictions. INTERNET just upgraded!

Nov 7 – 14

G$20,745 GYD per night

Condo in The Blue Mountains

4.89 out of 5 average rating, 350 reviews

Base of Blue Mountain, Modern Updated Studio

This gorgeous studio chalet is absolutely perfect for two, or a couple with small children! Newly renovated with a custom kitchen and fireplace. Located right at the base of the ski hill, our cozy chalet is a lovely fully furnished 1 bedroom, 1 bath. Blue Mountain Village only 1Km away, as well as the Scandinavia Spa , Northwinds Beach and restaurants. Our chalet is ski in ski out and located right at the North Chair. Come and enjoy all that Blue Mountain has to offer!

Sep 30 – Oct 7

G$27,164 GYD per night

Cabin in Mono

4.94 out of 5 average rating, 273 reviews

The Trails Retreat (Private Cabin)

Beautifully renovated 2-story private hilltop cabin for romantic getaway, family stay or friends' retreat, experience a taste of the country together. Backed by forest and trails and set away from our family home and yoga studio, minutes to the Bruce Trail, Hockley Ski & Resort, and Mansfield Ski Club, enjoy total guest privacy & spectacular sunrises. Guests are welcome to share our heated pool in season:) Chef's creations and Private yoga and group classes available

Feb 9 – 16

G$34,970 GYD per night

Farm stay in Markdale

4.99 out of 5 average rating, 124 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 when on the property.

Apr 7 – 14

G$29,918 GYD per night

Chalet in The Blue Mountains

4.94 out of 5 average rating, 293 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

Jul 12 – 19

G$34,349 GYD per night

Home in Kimberley

4.88 out of 5 average rating, 176 reviews

Heart of Kimberley - with views and a hot tub

Welcome to the hamlet of Kimberley nestled in the Beaver Valley. Surrounded by nature, the Rock House is a historic six bedroom century home with beautiful views close to many outdoor activities, and located beside an unassuming gourmet restaurant and a general store with fresh coffee and in-house sourdough bread. We are located 25 minutes from Blue Mountain and 2 minutes from Beaver Valley Ski Club.

Jul 8 – 15

G$73,924 GYD per night

Vacation rentals for every style

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Kick off your hiking boots at these rustic lodgings

Popular amenities for Grey Highlands rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in The Blue Mountains

4.95 out of 5 average rating, 148 reviews

Serene mountainside home View/Shuttle Bus/Pool

Nov 8 – 15

G$75,509 GYD per night

Home in The Blue Mountains

4.91 out of 5 average rating, 167 reviews

Views Mountains Sauna/Shuttle/Pool/Entertainment

Nov 3 – 10

G$48,269 GYD per night

Home in Owen Sound

4.98 out of 5 average rating, 214 reviews

The Butchart Estate: your perfect family retreat!

Nov 10 – 17

G$87,762 GYD per night

Home in Meaford

4.96 out of 5 average rating, 146 reviews

Redhill Luxury Home...by the Blue Mountains

Nov 2 – 9

G$159,246 GYD per night

Home in Chatsworth

4.88 out of 5 average rating, 130 reviews

Stonehaven - large country retreat, with pool*

Jan 8 – 15

G$109,671 GYD per night

Home in Collingwood

5.0 out of 5 average rating, 23 reviews

An oasis getaway near trails, lake, restaurants

May 27 – Jun 3

G$48,175 GYD per night

Home in Flesherton

4.85 out of 5 average rating, 13 reviews

Paul’s Pool House

Nov 25 – Dec 2

G$42,973 GYD per night

Home in The Blue Mountains

5.0 out of 5 average rating, 12 reviews

Spacious Condo next to The Blue Mountains w/ Patio

Nov 14 – 21

G$25,014 GYD per night

Condo rentals with a pool

Condo in The Blue Mountains

4.87 out of 5 average rating, 298 reviews

Ski in/out @ North Creek W King bed! New Hot Tub

Jul 2 – 9

G$36,243 GYD per night

Condo in The Blue Mountains

4.93 out of 5 average rating, 144 reviews

Mountainside Studio Bliss: Just Renovated, Tennis

May 16 – 23

G$28,603 GYD per night

Condo in The Blue Mountains

4.97 out of 5 average rating, 299 reviews

Gorgeous Two Bedroom Condo Overlooking Ski Hill

Aug 23 – 30

G$59,936 GYD per night

Condo in The Blue Mountains

4.95 out of 5 average rating, 207 reviews

Cozy & Charming Retreat at Blue Mountain

May 5 – 12

G$30,405 GYD per night

Condo in The Blue Mountains

4.97 out of 5 average rating, 126 reviews

Snowbridge Escape at Blue

Jan 7 – 14

G$39,532 GYD per night

Condo in The Blue Mountains

4.97 out of 5 average rating, 116 reviews

Rustic Chic Renovated 2Bd Condo by Village

Oct 5 – 12

G$42,817 GYD per night

Condo in The Blue Mountains

4.92 out of 5 average rating, 406 reviews

★Blue Mountain Village★ Cozy, Stylish, 360 Views

Oct 27 – Nov 3

G$40,542 GYD per night

Condo in Innisfil

4.97 out of 5 average rating, 111 reviews

•#TheFridayFlat Luxury Poolside Retreat for Summer

Oct 5 – 12

G$22,683 GYD per night

Quick stats about vacation rentals with a pool in Grey Highlands

Total rentals
440 properties
Rentals with dedicated workspaces
210 properties have a dedicated workspace
Pet-friendly rentals
130 properties allow pets
Family-friendly rentals
330 properties are a good fit for families
Total number of reviews
32K reviews
Nightly prices starting at
G$4,180 GYD before taxes and fees

Destinations to explore