House vacation rentals in Grey Highlands

Find and book unique houses on Airbnb

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$8,373 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.

1 of 1 pages1 / 1
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.

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

Top guest favorite
The exterior of a modern home is highlighted at sunset, showcasing large windows that reflect warm interior lighting. A spacious backyard features green grass, a dining area under a gazebo, and a hot tub on the deck, creating an inviting outdoor space.
Home in Barrie
4.97 out of 5 average rating, 152 reviews

Waterfront Home, City/Sunset View & Steps to Beach

Waterfront w/ private dock. Renovated upscale home + new hot tub, full city bay views w/summer sunsets+sunrise. Steps to Minet's Point beach & park. 4 proper bdrms & 2 pull out couches(Queen & Twin) 3 full bthrms + sauna, over 2400+sqft. Prking for 3 cars, additnal prking available via lot beside. Gas BBQ, fire pit, 2x gas FP, fast Wifi & 77" TV, wshr/dryr. 48amp EV pwr. Minutes to Marina for Seadoo/boat rentals. Wlking distnce to fine dining/pubs & stores. Kite surf & ice fishing

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.

Top guest favorite
The kitchen features modern cabinetry with blue and white accents. A marble countertop stretches across the kitchen island, which is complemented by a vibrant orange refrigerator. A dining area with a glass table and colorful stools offers a cheerful space for meals.
Home in Flesherton
4.98 out of 5 average rating, 44 reviews

Renovated 3-BR Home Near Old Baldy | BBQ & Hot Tub

Newly renovated chalet near Collingwood, Blue Mountain, and Eugenia Lake on a quiet paved road 🚴. Whether you love recreational activities, bird watching, relaxing in a hot tub, or cozying up by a wood-burning fire, this is a perfect place to be inspired by nature and unwind. Near by: - Beaver Valley Ski club - Hearts Tavern - Eugenia Lake - Old Baldy - Kolapore Trails - Metcalf Rock - Collingwood - Blue Mountains - Thornbury - The Roost Winery

Popular amenities for Grey Highlands house rentals

When is the best time to visit Grey Highlands?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$53,589 GYDG$48,774 GYDG$45,425 GYDG$37,261 GYDG$43,750 GYDG$44,169 GYDG$49,821 GYDG$53,170 GYDG$47,099 GYDG$44,797 GYDG$44,378 GYDG$57,566 GYD
Avg. temp-7°C-6°C-1°C6°C12°C17°C20°C19°C15°C9°C3°C-3°C

Destinations to explore

  1. Airbnb
  2. Canada
  3. Ontario
  4. Grey County
  5. Grey Highlands
  6. House rentals