
House holiday rentals in Grey Highlands
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Top-rated house rentals in Grey Highlands
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Decked in Old Hollywood Glam @ The Beachhouse POM
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

Close to Beach & Skiing with Large Fenced in Yard
Whether you are looking to rest and recharge or head out on an epic adventure in the hills, this comfortable century home is the perfect base. Nestled in the quaint town of Meaford the home is walking distance to everything you need for a great stay. It has a large backyard, fire area, patios, laundry, stocked kitchen & two living rooms. The recently updated home is set up perfectly for families & medium sized groups. The large fenced in backyard is perfect for pets and a great space for kids.

Large 4 Br - 4.5 Bathroom: 2 King beds/Sauna/games
Imagine a super large, cozy vacation home nestled in the heart of Blue Mountain Ski Resort, offering a perfect blend of luxury and comfort. Four bedrooms with 2 King beds. This expansive retreat boasts multiple levels to provide the utmost relaxation and tranquility. The home features 4.5 spacious bathrooms. Our Sauna and Entertainment basement is ready for guests' enjoyment. Walk to the Village or take a Free Shuttle Bus. Walk to Outdoor Heated Pool (Seasonal June-September) in 1 minute.

Kiss & Bond Water View Colpoys Bay 4 -Seasons
Hello,, I'm the owner of a newly built home, that I hope I will provide first-rate, memorable experiences for my guests, I'm a nurse for over 30 years, and I love to explore. Im an animals lover, I'm also a mother of 3 boys and have been married for 33 years ,being outdoors is one of my favourite activities, snowmobiling, hiking. I've owned our cottage for 10 years and we decided to rebuild , to enjoy the beautiful views of Colpoys Bay and in the back yard the Bruce Pennisula escarpment .

Adorable — One Bedroom Guest Unit in Vaughan, ON
Enjoy a stylish and peaceful stay at this centrally located one-bedroom lower-level unit, perfect for both leisure and business travelers. With your private entrance, parking, and all the essentials, it’s your ideal home away from home. Features include a full kitchen, bathroom, internet, smart TV, one Queen and one sofa bed, and a functional workspace. Steps from FreshCo, Walmart, restaurants, and services. Minutes to Vaughan Mills, Canada’s Wonderland, Cortellucci Hospital and transit.

Studio Apartment
Discover the perfect blend of comfort and convenience in this cozy studio apartment, ideally situated in the vibrant heart of Caledon. Key Features: Prime Location: Steps away from shops, cafes, and parks. Modern Amenities: Spacious living area, and stylish bathroom. Natural Light: Large windows that fill the space with warmth and brightness. Community Vibe: Enjoy the friendly neighborhood atmosphere and local events. This peaceful retreat, offers everything you need. Don't miss out!

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.

The Meaford Retreat! Beautiful Home on Wooded Lot.
Brand new upstairs bathroom. This beautiful Century home sits on a mature wooded lot less than a 1 min walk to a large conservation area with trails scenic in both summer and winter! Connect with nature whilst still being a 5 min walk from main street and harbour boasting shops, restaurants and trails. Close to Blue Mountains, Owen Sound, Thornbury and Collingwood. Hot Tub & Sauna available Fast WiFi 4 vehicle parking Front and back decks to enjoy your morning coffee. Beautiful!!

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. Minuts to Marina for Seadoo/boat rentals. Wlking distnce to fine dining/pubs & stores. Kite surf & ice fishing

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.

Serene mountainside home with View/Shuttle Bus
Welcome to this peaceful haven within the mountains. We have decorated our spacious and cozy home with comfortable beds, ample living amenities, and high-quality furniture to welcome you, your family and friends. Enjoy the carefully curated art pieces collected from around the world and look upon a stunning view of the snow-capped mountains from the master bedroom. Heated outdoor pool is seasonal! Walkable to the Village. Free Shuttle Bus

Williamsford Blacksmith Shop
Make some memories at the historic stone blacksmith shop built 1888. Located in Williamsford, Ontario. Conveniently located to the historic sites, waterfalls, the Bruce trail, rail trails for hiking and snowmobiling. Short 20 minute drive to Owen Sound. Sauble Beach 40 minutes. Tobermory drive 1 hr 1/2. Markdale 20 minutes. Enjoy the sites surrounding or a peaceful night by the campfire with campfire wood provided.
Popular amenities for Grey Highlands house rentals
House rentals with a pool

Cozy Corner Townhome | Shuttle To The Village

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

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

Blue Mountain Retreat In Historic Snowbridge

KickBack in Beautiful tranquil central condo

Charming One Bedroom at Snowbridge

Stonehaven - large country retreat, with pool*

Heart of Kimberley - with views and a hot tub
Weekly house rentals

Artists' House B&B: Exceptional Country Stay

Collingwood Resort Studio

Maple Forest Country Cottage

Walkerton Sauna Suite

Paradise in the Valley

Hillside Haven Retreat: Sunroom & Pond Escape

Entire Unit 2 bdr 2 bathroom | Full privacy

Balmy Beach Farm House
Private house rentals

Cottage Paradise - Water, Woods and Nature

Northwoods Ski Lodge - Georgian Bay Waterfront

The Cozy on Colborne

3 bedroom apartment

Cottage Escape on Lake Eugenia

5+ bdr Cottage Collingwood Blue Mountain Singhamp

Bright basement apt with private entrance, Barrie

Whites Junction Rural Retreat
When is the best time to visit Grey Highlands?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $315 AUD | $351 AUD | $298 AUD | $271 AUD | $318 AUD | $321 AUD | $362 AUD | $386 AUD | $342 AUD | $277 AUD | $256 AUD | $370 AUD |
| 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 house rentals in Grey Highlands

Total holiday rentals
Explore 250 holiday rentals in Grey Highlands

Nightly prices starting at
Grey Highlands holiday rentals start at $61 AUD per night before taxes and fees

Verified guest reviews
Over 7,480 verified reviews to help you choose

Family-friendly holiday rentals
230 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 110 rentals that welcome pets

Holiday rentals with a pool
60 properties feature pools

Rentals with dedicated workspaces
140 properties have a dedicated workspace

Wi-Fi availability
250 of Grey Highlands holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Grey Highlands rentals

4.9 Average rating
Grey Highlands stays are highly rated by guests—averaging 4.9 out of 5!
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- Blue Mountain Village
- Snow Valley Ski Resort
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- Beaver Valley Ski Club
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- Craigleith Ski Club
- Mount St. Louis Moonstone
- TPC Toronto at Osprey Valley
- The Georgian Peaks Club
- The Club At Bond Head
- Caledon Country Club
- The Georgian Bay Club
- Barrie Country Club
- Alpine Ski Club
- Toronto Ski Club
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- Springwater Golf Course
- Inglis Falls
- Heritage Hills Golf Club
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