
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.

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)

Blue Mountain Studio Retreat
Our cozy studio is located at the base of Blue Mountain at the North chair lift, with ski in / ski out access. Perfect for 2 or a couple with small children, this newly renovated Studio has 1 bedroom, 1 bathroom and sofa bed; fully stocked kitchen, electric fireplace and flat screen T.V. Only 1 km from the Village with many restaurants, shopping and activities. Enjoy a short trip to the Scandinavia Spa or many close by beaches. Blue Mountain is a great place for the whole family to enjoy.

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.

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, minutes to the Bruce Trail, Hockley Ski & Golf Resort, Mansfield Ski Club and charming Orangeville. Enjoy total guest privacy & spectacular sunrises. Guests are welcome to share our heated pool in season:) Add a playful Yoga/Functional Movement class or chef's dinner to your stay!

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

Woodski Winter Haven: Mountain Cottage Near Skiing
This private mountain retreat is just 15 minutes from Blue Mountain, features 3.2 acres of beautiful scenery, a swimming pool and a renovated home for 10 guests (Max 8 adults). The house sits at the foot of a private 500ft mountain that is yours to explore all year around. Inside, there is a spacious home built for entertainment. Enjoy all-year fun at the property or head out to enjoy the amazing activities nearby. Only 5 minutes to the beach and 15 minutes to the best skiing in Ontario!

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.

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.

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.

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)

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.

BLUE MOUNTAIN STUDIO OASIS
-Private Newly Updated Studio -WIFI and Smart TV -Ski in/Ski out with outdoor locker -Fireplace -Full Kitchen, Full Bath -Sleeps up to 4 (Queen Bed and Pull Out Couch) -Free Shuttle to the Village -1 km from Northwinds Beach -Outdoor shared hot tub (Open) Seasonal Pool (Open May24-Labour Day 10am-8pm) UNSUPERVISED -Tennis Courts -Free Parking -Walk to Village (1.4km) & Trails -Shared BBQ’s, bring charcoal *No parties STA LICENCE #-LCSTR20220000083
Popular amenities for Grey Highlands rentals with a pool
House rentals with a pool

Cozy Corner Townhome | Shuttle To The Village

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

King Bed, Pool, Gym, Ravine View, Your Getaway!

Luxurious 4BDRM-King Bed-Barrie-near Snow Resorts

Blue Mountain Retreat In Historic Snowbridge

Serene mountainside home with View/Shuttle Bus

Stonehaven - large country retreat, with pool*

Heart of Kimberley - with views and a hot tub
Condo rentals with a pool

Spacious 1-br w jacuzzi at Horseshoe Valley

Blue Mountain condo in Historic Snowbridge

Cozy Studio Mountainside stay in Blue Mountains

Still Winds Ski Chalet | Free Shuttle To Blue

Base of Blue Mountain, Modern Studio

3 Peaks at Blue Mountains, your luxury staycation!

Highlands Lodge & Loft - Shuttle to the Village

Cozy & Charming Retreat at Blue Mountain
Other vacation rentals with a pool

Farmhouse GUEST SUITE; Year round hot tub

The Snowbridge Lookout on Monterra Golf Course

Experience Country Living at Firefly Ridge

Ski In/Ski Out & Hot Tub 2 Bedroom, 2 floor home

KickBack in Beautiful tranquil central condo

Blue Mountain Village Townhome 4 Bedroom w Shuttle

Blue Mountain Escape! Pool&HotTub. Walk to Village

Waterfront Cottage #2
When is the best time to visit Grey Highlands?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$30,128 GYD | G$31,802 GYD | G$28,245 GYD | G$23,224 GYD | G$24,479 GYD | G$26,362 GYD | G$31,593 GYD | G$32,639 GYD | G$22,596 GYD | G$26,362 GYD | G$22,596 GYD | G$33,057 GYD |
| Avg. temp | -7°C | -6°C | -1°C | 6°C | 12°C | 17°C | 20°C | 19°C | 15°C | 9°C | 3°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 G$8,369 GYD 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 & kid-friendly amenities

Pet-friendly vacation rentals
Find 150 rentals that welcome pets

Rentals with dedicated workspaces
300 properties have a dedicated workspace

Wi-Fi availability
490 of Grey Highlands vacation 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!
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- Blue Mountain Village
- Snow Valley Ski Resort
- Cobble Beach Golf Resort Community
- Beaver Valley Ski Club
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- TPC Toronto at Osprey Valley
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