
Holiday rentals with a pool in Grey Highlands
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Top-rated rentals with a pool in Grey Highlands
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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

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

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

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.

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

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

Cozy Beach Cottage with Pool | Georgian Bay
Georgian Bay Beach club. Cute cottage perfect for families, couples, or anyone wanting to relax! 2 bedrooms, 1 bathroom, furnished, pool and private beach on the shores of beautiful Georgian Bay in Tiny township. Cottage is part of a 12 cottage community that shares the pool and beach area. Always super clean, professionally cleaned after every guest! Note: pool is closed October to mid May.

Cozy getaway for two with hot tub!
Unwind in our peaceful guest suite attached to our home located near Mount St-Louis Moonstone, Vetta Nordic Spa and the cozy town of Coldwater. With its private entrance, hot tub (accessible daily between 8am and 10pm) and serene forest surroundings, this space is designed for guests who value calm, quiet and nature. We ask that guests share our appreciation for a tranquil environment.

Mountainside Escape | Ski-In-Out, Shuttle, Hot Tub
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 the spring and summer months.

Tranquility Oasis Ski-In Out, Hot Tub, Shuttle
Tranquility Oasis 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 the spring and summer months.
Popular amenities for Grey Highlands rentals with a pool
House rentals with a pool

Cozy Corner Townhome | Shuttle To The Village

New look The Greenview Retreat

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

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

Blue Mountain Village Townhome 4 Bedroom w Shuttle

Stonehaven - large country retreat, with pool*

Heart of Kimberley - with views and a hot tub

Chic King West Studio – TIFF & FIFA at Your Door
Condo rentals with a pool

Lovely 3 Bedroom Condo with Stunning View and Pool

Blue Mountain condo in Historic Snowbridge

Large 3BR Modern Luxury Escape | Walk to Blue

Explore a Winter Wonderland at Blue Mountain

Cozy Studio Mountainside stay in Blue Mountains

Base of Blue Mountain, Modern Studio

Highlands Lodge & Loft - Shuttle to the Village

Hidden gem in Humber bay shores Toronto w/ parking
Other holiday rentals with a pool

Experience Country Living at Firefly Ridge

HotTub & Cozy Fireplace - Headwaters Retreat

3BR Sierra Scandi Chic - Closest to Village

Cosy Chalet - 4 Season Family Oasis

The Trails Retreat (Private Cabin)

Four season glamping dome under the stars

Sierra Views - Steps to Blue Mountain Village!

Gorgeous Two Bedroom Condo Overlooking Ski Hill
When is the best time to visit Grey Highlands?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $241 NZD | $254 NZD | $226 NZD | $186 NZD | $196 NZD | $211 NZD | $253 NZD | $261 NZD | $181 NZD | $196 NZD | $189 NZD | $288 NZD |
| 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 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 $84 NZD 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!
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- Blue Mountain Village
- Snow Valley Ski Resort
- Mount St. Louis Moonstone
- Beaver Valley Ski Club
- Wasaga Beach Area
- Osler Bluff Ski Club
- Devil's Glen Country Club
- Scandinave Spa Blue Mountain
- Elora Gorge
- Inglis Falls
- Caledon Ski Club LTD
- Harrison Park
- Elora Quarry Conservation Area
- Forks of the Credit Provincial Park
- Wye Marsh Wildlife Centre
- Sauble Beach
- Mono Cliffs Provincial Park
- Innisfil Beach Park
- Awenda Provincial Park
- Centennial Beach
- Sunset Point Park
- Rockwood Conservation Area
- Island Lake Conservation Area
- Sauble Falls Provincial Park




