House vacation rentals in Grey Highlands

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Quick stats about house rentals in Grey Highlands

  • Total vacation rentals

    Explore 270 vacation rentals in Grey Highlands

  • Nightly prices starting at

    Grey Highlands vacation rentals start at G$8,365 GYD per night before taxes and fees

  • Verified guest reviews

    Over 9,000 verified reviews to help you choose

  • Family-friendly vacation rentals

    240 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 130 rentals that welcome pets

  • Vacation rentals with a pool

    70 properties feature pools

  • Rentals with dedicated workspaces

    150 properties have a dedicated workspace

  • Wi-Fi availability

    270 of Grey Highlands vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Grey Highlands rentals

  • 4.9 Average rating

    Grey Highlands stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated house rentals in Grey Highlands

Guests agree: these houses are highly rated for location, cleanliness, and more.

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Guest favorite
The image captures a tranquil hot tub filled with clear water, positioned on a deck overlooking Georgian Bay. A soft sunset casts a warm glow across the sky, and the silhouettes of a gazebo and dock are visible in the background.
Home in Meaford
4.87 out of 5 average rating, 536 reviews

Beach House Hideaway by Post Office Motel *HOT TUB

This beach house was designed with relaxation and the enjoyment of togetherness in mind. Let your worries melt away as you slip into the warmth of this water side hot tub featuring stunning view across Georgian Bay and up the mountain side, as fresh snow falls around you. The open concept design makes this the perfect place to gather with family and friends w/ walkout waterfront patio and dock access for swimming. 2 min to downtown Meaford, 20 min to Blue Mtn, 1.5 hrs to Tobermory. Hiking Trails

Top guest favorite
A spacious dining area features a large wooden table set for eight, surrounded by black chairs. A modern chandelier hangs above, illuminating the setting. Large windows offer views of the outdoors, allowing natural light to fill the space.
Home in Kimberley
5 out of 5 average rating, 50 reviews

Beaver Valley Vista: Secluded w Hot Tub, Fire Pit

Welcome to Valley View Cottage! Nestled in the heart of nature, this retreat offers a picturesque escape. With four cozy bedrooms, relaxing hot tub, and a mesmerizing fire pit, it's the perfect getaway. Immerse yourself in the beauty of the valley, explore nearby hiking trails, or simply unwind in the comfort of our rustic yet modern cottage. ✔ 4 Comfy Bedrooms ✔ Open Design Living ✔ Fully Equipped Kitchen ✔ Fire Pit, Balcony, Hot Tub ✔ Pool table, dart board, ping pong table Learn more below!

Top guest favorite
Home in Collingwood
4.93 out of 5 average rating, 110 reviews

The Artist's House B&B: Relax, Explore Collingwood

Welcome to The Artist's House — a charming getaway in the village of Nottawa, just minutes from Blue Mountain, Collingwood, Scandinave Spa, and Georgian Bay beaches. Surrounded by beautiful gardens, sculpture, and original artwork, our home offers three serene bedrooms, air conditioning, a fully equipped kitchen, and a cozy living room with gas fireplace. Relax on the patio, enjoy the BBQ and fire pit, and experience the perfect blend of village charm and nearby adventure. Fast Wi-Fi & parking.

Guest favorite
A sunlit living area is presented with large windows overlooking a snowy landscape. Comfortable seating is arranged around a wooden coffee table. Light walls are complemented by natural wood accents and a colorful rug adds a touch of warmth to the space.
Home in Meaford
4.97 out of 5 average rating, 178 reviews

Redhill Luxury Home...by the Blue Mountains

This eco friendly house of 4,500 sq ft is bright, modern, luxurious on 50 acres of rolling hills with a beautiful pond and hiking trails. All bedroom ensuite plus 2 extra full bathrooms. Comfortably sleeps up to 24 guests. Amazing view, sunset and star gazing. Salt water pool in the summer. Outdoor BBQ, fire pit, Hot Tub April to Nov. Minutes to Christie beach, ski hills, golf courses, Bruce Trail. Enjoy snowshoeing, cross country. Serenity on top of the hill! See more info under the space.

Top guest favorite
An open and airy space features a large harvest table with pink legs, complemented by wooden chairs. A cozy bench is positioned alongside the table. A staircase leads to a loft area, while art supplies and decor are visible throughout the room.
Home in Desboro
4.96 out of 5 average rating, 141 reviews

Forest Loft - Forest, Sauna, Ponds & Stargazing

The “Forest Loft” is a one-of-a-kind space surrounded by the old-growth trees of Kinghurst Forest. The 1,600-square-foot space sleeps up to four and features two Queen-size beds and linens, huge harvest table, indoor kitchenette with a stovetop and fridge, filtered water, shower, propane and wood stove heating, in-door basketball hoop, hammock, picnic table, a commercial grade BBQ, fire ring and access to two beautiful spring-fed ponds. Access to Finnish sauna for four is available on request.

Guest favorite
An open concept game room features a polished pool table at the center, with a bar area equipped with stools to one side. Large windows allow natural light to fill the space, while a mounted TV and comfortable sectional couch create an inviting entertainment area.
Home in Badjeros
4.94 out of 5 average rating, 187 reviews

JJ’s small town country retreat

Take a step back in time to this old farm house. Located on the corner of our little town called Badjeros. This house was built in the 1930s and it’s been in our family for over 80 years. Since then there has been numerous upgrades to the house as well as a large 1200 square foot open concept addition built onto the existing house. While out in the country, this house is central to many attractions in the area 1.5 hours south of Toronto/GTA. Blue Mountain/ Collingwood is 30 minutes north.

Top guest favorite
An open game room features a polished wooden pool table at its center, surrounded by exposed timber beams and vibrant green walls. Large windows provide natural light, while a television is mounted nearby. Additional seating is available, enhancing the space's social atmosphere.
Home in Meaford
4.98 out of 5 average rating, 111 reviews

Birdsong, the perfect Blue Mountains getaway

Welcome to Birdsong: a lavishly comfortable, highly unique, year-round space designed with an eye for the eclectic and enjoyable. This enchanting vacation property boasts an enormous hot tub that doubles as a heated indoor pool; as well as a sauna, well-equipped boutique gym, pool table, dedicated conference room/business center, outdoor fire pit and treehouse for kids. Surrounded by the gorgeous Blue Mountains, Birdsong is the perfect ski season rental; as well as summer family getaway.

Top guest favorite
Home in West Grey
5 out of 5 average rating, 19 reviews

Woodland River Retreat With Hot Tub

Welcome to this modern, stylish and private cottage escape. Located on the beautiful Saugeen River in the picturesque village of Glenelg Centre, Grey County this cozy cottage offers up private accommodations in a forest setting with sweeping river views. If you're looking for privacy and tranquility along with all the pleasures of a luxury stay then look no further. Fully equipped kitchen, two bedrooms with hotel quality mattresses and a bathroom that exudes high-end style and decor.

Guest favorite
Home in Collingwood
4.86 out of 5 average rating, 326 reviews

Bright & Spacious Family Home Close to Ski Hill

Bright & spacious 5 bedroom home located in the heart of Collingwood. Walking distance to the waterfront, walking trails, local restaurants, grocery stores and only 6 mins away from Blue Mountain Village. The house features two separate living room spaces. The beautiful open concept kitchen & living room has vaulted ceilings and lots of natural light. A perfect gathering place for families or multiple couples. 6 snowboards, boots for men, one canoe and two bicycles free of charge

Guest favorite
Home in Flesherton
4.87 out of 5 average rating, 15 reviews

The Hidden Haven Cottage

Relax, have fun and make memories with the whole family, pups included, at this peaceful lakefront cottage. The cottage, located on Eugenia Lake, boasts floor-to-ceiling windows, a fully equipped kitchen, four bedrooms with luxury linens, cozy fireplaces, and an assortment of outdoor activities, including a dock, firepit, hammock, paddleboards, kayaks, and a canoe. With numerous conservation areas and Bruce Trail access points in the vicinity, there's truly something for everyone.

Top guest favorite
Home in Meaford
4.99 out of 5 average rating, 106 reviews

Stonefox Retreat: Acerage, Pond, Hot Tub & Sauna

This stunning century home has been family-owned for over 50 years. A limestone cottage built in 1850 with a modern addition this is a huge house on an entirely secluded acarage with a lake-sized swimming pond with floaties and a dock. A true escape through time, but with modern amenities, this property is loved by all ages. There is ample room to gather and to retreat. It's a perfect choice for families and / or groups of friends to get together in their own private world.

Guest favorite
Home in Collingwood
4.92 out of 5 average rating, 113 reviews

Cozy Collingwood Farm Retreat

Welcome to this very private 2 bedroom home located on a fenced-in 10 acre property that is located just 3 minutes to downtown Collingwood, and 10 minutes to Blue Mountain. Come and relax here after a day on the slopes or hiking trails , and enjoy the warmly decorated living room with a wood stove! Perfect property all to yourself to enjoy ultimate privacy while still being in town and close to everything! Bring the pooch and enjoy everything this property has to offer.

Popular amenities for Grey Highlands house rentals

When is the best time to visit Grey Highlands?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$53,538 GYDG$48,728 GYDG$45,382 GYDG$37,226 GYDG$43,709 GYDG$44,127 GYDG$49,773 GYDG$53,120 GYDG$47,055 GYDG$44,754 GYDG$44,336 GYDG$57,511 GYD
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