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.

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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, 315 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 cozy sleeping area is highlighted by a black wooden bed frame with a crisp white bedding set. Decorative pillows are arranged on the bed, while a framed image of a bear adorns the wall. Soft bedside lighting is provided by sconces, complementing the mirror opposite.
Flat in Blue Mountain Resort Area
4.91 out of 5 average rating, 178 reviews

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.

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

Top guest favourite
A spacious living area features tall windows allowing natural light to fill the room. A large screen TV is mounted above a gas fireplace, surrounded by comfortable seating. Decorative pillows enhance the sectional sofa, and an elegant coffee table sits centrally, adding to the inviting atmosphere.
Townhouse in Blue Mountain Resort Area
4.97 out of 5 average rating, 237 reviews

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

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 home in Meaford
4.86 out of 5 average rating, 408 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.

Guest favourite
A cozy family room features a spacious gray sectional sofa and a wooden coffee table. Light-colored walls and a patterned rug create a welcoming atmosphere. In the background, a kitchen area is visible, equipped with modern appliances and seating for two.
Apartment in Blue Mountain Resort Area
4.93 out of 5 average rating, 321 reviews

Cozy Studio Mountainside stay in Blue Mountains

Enjoy Winter now in the Blue Mountains. Book your getaway now. This cozy STUDIO ground floor condo is perfect for a couple/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. Hot tub is open daily. Access to the North side of Blue from our condo. Blue Mountain Village is only a 5 minute drive away (20 min walk) with great local restaurants and shops.

Guest favourite
The open concept living area features a modern sofa and armchair arranged around a glass coffee table. A gas fireplace is centered on the wall beneath a mounted TV. Light streams through large windows, illuminating the space.
Apartment in Blue Mountain Resort Area
4.88 out of 5 average rating, 283 reviews

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.

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.
Flat in Blue Mountain Resort Area
4.96 out of 5 average rating, 351 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)

Guest favourite
A spacious living area features a modern fireplace with a stone surround and a wall-mounted flat-screen TV. A small blue chair complements the neutral tones, while the open kitchen includes a breakfast bar with two high stools. Natural light enters through the window, illuminating the room.
Apartment in Blue Mountain Resort Area
4.85 out of 5 average rating, 114 reviews

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

Guest favourite
Cottage in Lafontaine
4.84 out of 5 average rating, 271 reviews

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.

Top guest favourite
A spacious living area features a modern kitchen with stainless steel appliances and light cabinetry. A comfortable sofa is paired with a low coffee table, adorned with greenery. Natural light flows in through large windows, enhancing the inviting space.
Flat in Coldwater
4.97 out of 5 average rating, 125 reviews

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.

Guest favourite
A cozy living area is presented with two sofas and a fabric armchair, arranged around a wooden coffee table. A gas fireplace sits beneath a wall-mounted television. Large windows allow natural light, offering views of the surrounding landscape.
Apartment in Blue Mountain Resort Area
4.93 out of 5 average rating, 281 reviews

The Blue Mountain's Dream Escape | Pool | Hot Tub

The Blue Mountain's Dream Escape is here for your perfect family getaway. Wake up to a great view of beautiful Blue Mountains and Monterra golf course. Village is just 5-7 minute walk or 1 min drive. Our ground floor end unit condo has everything you need for a perfect stay. PLEASE NOTE: - Hot tub is open year round - Pool is closed for the season

Popular amenities for Grey Highlands rentals with a pool

When is the best time to visit Grey Highlands?

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Avg. price$182 SGD$193 SGD$171 SGD$141 SGD$148 SGD$160 SGD$191 SGD$198 SGD$137 SGD$148 SGD$143 SGD$218 SGD
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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 $63 SGD 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 & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 150 rentals that welcome pets

  • Rentals with dedicated workspaces

    290 properties have a dedicated workspace

  • Wifi availability

    480 of Grey Highlands holiday 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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