Grey Highlands holiday rentals

We found 1,019 holiday rentals — enter your dates for availability
Select from 34 homes, 21 cottages and other holiday rentals in Grey Highlands to find one that's perfect for your trip. Whether you're travelling with your children and pets, with friends or just your children, holiday homes have the amenities that you expect for your stay, which might include parking and a pool. No matter what you're looking for, you're sure to find a property to rent to meet everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Grey Highlands

Showing deals for:18 Dec - 25 Dec

Dinner Table
Living Area - Main floor
Living Area
Property grounds
Exceptional
(8 reviews)

Shale Beach House -- 5 minutes drive to Blue Mountain Village!

The Blue Mountains

7% off
AU$8,515
for 7 nights, 1 chalet
AU$1,216 per night
includes taxes & fees
Shale Beach House -- 5 minutes drive to Blue Mountain Village!
Dinning area - Unit 2
Interior
Stair to lower Level
Interior
Exceptional
(7 reviews)

Legend Cottages(Sleep40) - indoor Pool & hot tub & Sauna

The Blue Mountains

8% off
AU$27,273
for 7 nights, 1 chalet
AU$3,896 per night
includes taxes & fees
Legend Cottages(Sleep40) - indoor Pool & hot tub & Sauna
Interior
Private kitchen
Dining
Living area
Exceptional
(6 reviews)

Canyon Connection Chalet - Pool Table + Mountain View!

The Blue Mountains

20% off
AU$6,722
for 7 nights, 1 chalet
AU$960 per night
includes taxes & fees
Canyon Connection Chalet - Pool Table + Mountain View!
Living area
Interior
Living area
Private kitchen
Exceptional
(16 reviews)

Enjoy the beautiful Getaway chalet and all the outdoor activities at Irish Lake!

West Grey

8% off
AU$3,000
for 7 nights, 1 chalet
AU$429 per night
includes taxes & fees
Enjoy the beautiful Getaway chalet and all the outdoor activities at Irish Lake!
Room
Dining
Mainfloor walk-out balcony.
Private kitchen
Exceptional
(13 reviews)

Modern Industrial Getaway - 1 minute walk to the Beach & Boat Launch

Grey Highlands

8% off
AU$4,401
for 7 nights, 1 home
AU$629 per night
includes taxes & fees
Modern Industrial Getaway - 1 minute walk to the Beach & Boat Launch
sun room with double sofa bed
Outdoor dining
Pool
Private kitchen
Exceptional
(7 reviews)

Grand Luxury Cottage by Blue Mountains with pool and hot tub

Meaford

8% off
AU$11,465
for 7 nights, 1 cottage
AU$1,638 per night
includes taxes & fees
Grand Luxury Cottage by Blue Mountains with pool and hot tub
Private kitchen
Living area
Room
Dining
Exceptional
(10 reviews)

Secluded 3BR A-Frame on 25 Private Acres w/ Trails, Fireplaces & Soaker Tub

Chatsworth

8% off
AU$3,142
for 7 nights, 1 home
AU$449 per night
includes taxes & fees
Secluded 3BR A-Frame on 25 Private Acres w/ Trails, Fireplaces & Soaker Tub
Dining
Private kitchen
Living area
Exterior
Exceptional
(7 reviews)

BLUE MOUNTAIN CHALET w/Hot Tub & Fire Pit. Pet friendly!

The Blue Mountains

25% off
AU$8,575
for 7 nights, 1 chalet
AU$1,225 per night
includes taxes & fees
BLUE MOUNTAIN CHALET w/Hot Tub & Fire Pit. Pet friendly!
Pull out couch for extra sleep space
We are on the ground floor- fully contained condo (no sharing with neighbors)
View of the mountain from the front door!
View from the bedroom
Wonderful
(17 reviews)

Private Backyard/Shuttle/Pool/10min walk to the Village

The Blue Mountains

5% off
AU$1,943
for 7 nights, 1 home
AU$278 per night
includes taxes & fees
Private Backyard/Shuttle/Pool/10min walk to the Village
Interior
Living area
Room
Private kitchen
Exceptional
(19 reviews)

Woodland Edge (7 bedrooms+Hot Tub+Heated Pool for summer)

The Blue Mountains

8% off
AU$12,664
for 7 nights, 1 chalet
AU$1,809 per night
includes taxes & fees
Woodland Edge (7 bedrooms+Hot Tub+Heated Pool for summer)
Dining
Private kitchen
Interior
Interior
Wonderful
(22 reviews)

Rightview Heaven (10 bedrooms + Private Hot Tub)

The Blue Mountains

8% off
AU$13,269
for 7 nights, 1 chalet
AU$1,896 per night
includes taxes & fees
Rightview Heaven (10 bedrooms + Private Hot Tub)
Dinning area
Sitting Area - Upper Level
Pool
Sitting area - Upper Level
Wonderful
(10 reviews)

Indoor heated pool and Sauna- 8 Bedroom Chalet "Left Bank Onsis" @ Blue Mountain

The Blue Mountains

8% off
AU$13,904
for 7 nights, 1 chalet
AU$1,986 per night
includes taxes & fees
Indoor heated pool and Sauna- 8 Bedroom Chalet "Left Bank Onsis" @ Blue Mountain
Private kitchen
Room
Exterior
Exterior
Exceptional
(7 reviews)

K's Cozy Condo -Mins. to Beach, Trails, Shops, Skiing. Walk to restaurants, bar.

Collingwood

7% off
AU$2,194
for 7 nights, 1 apartment
AU$313 per night
includes taxes & fees
K's Cozy Condo -Mins. to Beach, Trails, Shops, Skiing. Walk to restaurants, bar.
Dining Area
Interior
Fireplace and TV - Living Area
Living Area
Exceptional
(95 reviews)

Family-friendly Modern Home less than 5 min walk to Ski & Village! Sleeps 8

The Blue Mountains

8% off
AU$6,757
for 7 nights, 1 home
AU$965 per night
includes taxes & fees
Family-friendly Modern Home less than 5 min walk to Ski & Village! Sleeps 8

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Delight in the natural landscape of Grey Highlands

The waterfalls, wildlife and forests are the perfect backdrop to your holiday home in Grey Highlands. Travellers appreciate the hiking in this welcoming city. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in Grey Highlands

Do you want to discover attractions to see while you're in town? Venture out of your holiday home and experience everything that Grey Highlands has to offer. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Blue Mountain Ski Resort (16.9 mi / 27.2 km)
  • Beaver Valley Ski Club (1.9 mi / 3 km)
  • Georgian Hills Vineyards (13.2 mi / 21.2 km)
  • Lora Bay Golf Club (16.6 mi / 26.7 km)
  • Ridge Runner Mountain Coaster (17.2 mi / 27.6 km)
  • Plunge Aquatic Center (17.2 mi / 27.7 km)

Exploring the natural features in Grey Highlands

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Grey Highlands is a great spot to appreciate mother nature. These are some of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • Eugenia Falls Conservation Area (4 mi / 6.5 km)
  • Eugenia Lake (4.8 mi / 7.7 km)
  • Blue Mountain Beach (16.4 mi / 26.4 km)
  • Collingwood Scenic Caves (16.5 mi / 26.5 km)
  • Scenic Caves Nature Adventures (16.5 mi / 26.5 km)
  • Bruce Trail Lookout (16.6 mi / 26.7 km)

Frequently asked questions

What is the best area to stay in Grey Highlands when booking a holiday rental?
When considering a holiday rental in Grey Highlands, Ontario, a popular area to stay is around the charming village of Flesherton. This picturesque community offers a delightful blend of natural beauty and local culture, making it an ideal spot for visitors. The area is known for its proximity to the stunning Eugenia Falls Provincial Park, where you can enjoy scenic hiking trails and breathtaking views. Additionally, the nearby Beaver Valley is a fantastic destination for outdoor enthusiasts, offering opportunities for skiing in the winter and hiking in the warmer months.Flesherton features a variety of rental properties, from quaint cottages to more spacious homes, suiting different group sizes and preferences. The village is also home to several unique shops and eateries, providing a taste of local flavour that enhances your stay. Another appealing aspect of the region is its community spirit, with various events and festivals happening throughout the year, ensuring that there's always something to enjoy during your visit.
Where are the best areas for renting a beach house in Grey Highlands?
For renting a beach house in Grey Highlands, the area around the scenic shores of Lake Eugenia is a prime choice. This picturesque lake offers a variety of holiday rentals, including charming cottages and modern homes that often come with amenities such as private docks, outdoor seating areas, and fully equipped kitchens. Many properties boast stunning views of the water, providing a superb backdrop for relaxation and outdoor activities.Additionally, the nearby Beaver Valley is known for its beautiful landscapes and recreational opportunities. Here, visitors can find rentals that feature amenities like hot tubs, fire pits, and access to hiking trails. Properties in this region typically cater to families or groups looking to explore the natural beauty of the area while enjoying comfortable accommodations.The town of Flesherton, with its quaint shops and local dining options, is also in proximity, enhancing the convenience for travellers seeking a beach getaway.
Where are the best Grey Highlands ski resort rentals?
For the best ski resort rentals in Grey Highlands, Ontario, travellers should consider the areas surrounding the Beaver Valley Ski Club and the nearby Blue Mountain region. The charming town of Flesherton offers a variety of rental options, including cosy chalets and family-friendly cabins that provide direct access to the ski slopes. Many of these properties come equipped with essential amenities such as fully stocked kitchens, spacious living areas with fireplaces, and outdoor decks for enjoying the serene winter landscape.In the Blue Mountain area, which is just a short drive from Grey Highlands, visitors can find a range of modern condos and lodges that cater to ski enthusiasts. These accommodations often feature amenities like ski-in/ski-out access, heated pools, fitness centres, and on-site dining options, providing convenience and comfort after a day on the slopes. Additionally, many properties include amenities such as hot tubs, superb for unwinding in the evenings.For those looking to explore the surrounding natural beauty, the Grey Highlands region offers numerous hiking and snowshoeing trails during the winter months. Properties located near the scenic Beaver Valley provide access to breathtaking views and opportunities for outdoor activities, enhancing the overall experience for travellers.
What is the most popular type of holiday rental accomodation in Grey Highlands?
In Grey Highlands, holiday houses are the most popular type of holiday rental, with approximately 63 available across the picturesque region. These properties are typically situated in serene areas, superb for those looking to enjoy the beautiful natural surroundings. Most holiday houses feature spacious layouts, multiple bedrooms, fully equipped kitchens, and often outdoor spaces such as decks or patios for relaxation after a day of exploring.Cottages also have a significant presence, with around 60 options that provide a charming and rustic experience. Similar to holiday houses, cottages usually come with essential amenities, including kitchen facilities and comfortable living areas. For those seeking a more unique stay, there are about 30 chalets available, which often boast alpine-style architecture and can include features like fireplaces and stunning views.Additionally, there are several apartments and cabins scattered throughout Grey Highlands, suiting various traveller preferences and group sizes.
Are there any family house rentals in Grey Highlands?
In Grey Highlands, Ontario, there are a variety of family-friendly house rentals available, with around 33 options to choose from. This area is renowned for its stunning natural landscapes, making it an excellent choice for families looking to enjoy outdoor activities. Many of these properties come equipped with spacious living areas, full kitchens for preparing meals together, and large outdoor spaces where children can play and explore.Visitors can find homes with amenities such as private patios, fire pits, and sometimes even hot tubs, great for unwinding after a day of adventure. The locale is also close to attractions like the scenic Beaver Valley, ideal for hiking, biking, and even skiing in the winter months. Furthermore, nearby parks offer playgrounds and picnic areas, ensuring that families have plenty of options for fun and relaxation.
Can I rent a holiday home with a pool or hot tub in Grey Highlands?
In Grey Highlands, Ontario, there are several holiday homes available for rent that feature pools or hot tubs, making it a delightful destination for relaxation and enjoyment. The area is known for its beautiful natural landscapes, with properties often located near scenic spots such as the Beaver Valley and the picturesque hills of the region. Many of these rentals offer amenities like private pools, hot tubs, spacious outdoor areas, and well-equipped kitchens, superb for family gatherings or retreats with friends. Additionally, some homes may include fireplaces and game rooms, enhancing the comfort and entertainment options during your stay.
Are there pet-friendly house rentals in Grey Highlands?
In Grey Highlands, there are a variety of pet-friendly house rentals available, with around 28 options for travellers to choose from. This charming area in Ontario is known for its picturesque landscapes and outdoor activities, making it an excellent destination for those travelling with pets. Many of the holiday rentals in Grey Highlands come equipped with amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces where pets can roam freely.The region offers easy access to stunning natural attractions like the Beaver Valley and the numerous hiking trails that wind through the beautiful scenery. Additionally, pet owners will appreciate the proximity to various parks and open spaces where their furry friends can enjoy the great outdoors.
Are there any remote work holiday rentals in Grey Highlands?
In Grey Highlands, Ontario, there are plenty of options for remote work holiday rentals, with around 132 available throughout the area. This picturesque region, known for its scenic landscapes and outdoor activities, is ideal for those looking to balance work and leisure. Many of the properties come equipped with essential amenities such as high-speed Wi-Fi, dedicated workspaces, and comfortable desk chairs, making it easy to stay productive while enjoying a tranquil setting.Travellers can expect a range of accommodations, from cozy cabins to spacious homes, often featuring fully equipped kitchens for self-catering and outdoor spaces to unwind after a day of work. The area is also well-suited for nature lovers, with nearby hiking trails and parks offering opportunities for relaxation and exploration during breaks. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Grey Highlands?
In Grey Highlands, popular rental amenities include well-equipped kitchens, superb for those who enjoy cooking during their stay. Many properties feature inviting fireplaces, adding a cosy atmosphere, especially during the colder months. Onsite parking is commonly available, making it convenient for guests arriving by car. Most rentals also offer decks or patios, allowing visitors to take in the picturesque surroundings while enjoying their morning coffee or tea, with many places providing a coffee or tea maker for added convenience.
When is the best time to visit Grey Highlands for a holiday rental?
The best time to visit Grey Highlands for a holiday rental is during the peak season from December to February. This period attracts winter enthusiasts who flock to the area for its exhilarating outdoor activities, such as skiing and snowboarding at local resorts. With a blanket of snow covering the landscape, visitors can enjoy picturesque winter scenery and a range of winter sports, making it an ideal time for adventure seekers.February, in particular, is a standout month, as it typically boasts chilly temperatures ranging from -5 to -10 degrees Celsius, creating superb conditions for a variety of snow activities. The vibrant setting during this month is palpable, with many fellow travellers sharing in the excitement of winter sports and cozy evenings by the fire.If you're considering a more budget-friendly option, May is a fantastic time to visit Grey Highlands. This month sees fewer tourists, allowing for a more tranquil experience as you explore the beautiful hiking trails and lush green landscapes that spring brings. You can enjoy the stunning natural beauty and peaceful surroundings without the hustle and bustle of the peak season.
What are the top attractions in Grey Highlands?
In Grey Highlands, visitors can discover a variety of attractions that highlight the region's natural beauty and outdoor activities. The Beaver Valley, known for its stunning landscapes, offers opportunities for hiking, cycling, and exploring scenic trails. The area is particularly popular during the fall when the foliage transforms into vibrant colours.For those interested in winter sports, the Blue Mountain Resort is nearby, providing skiing and snowboarding options, along with winter hiking trails.Additionally, the charming town of Flesherton features quaint shops and eateries, while the Grey Highlands Arts Council often hosts local art exhibitions that showcase the talents of regional artists.
Are all fees included in the Grey Highlands holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Grey Highlands holiday homes with parking?
Stayz offers a wide selection of holiday homes in Grey Highlands with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Grey Highlands holiday homes?
You can find great discounts on holiday homes in Grey Highlands on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Grey Highlands holiday home booking on Stayz?
To find Grey Highlands holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Grey Highlands?
A long-stay holiday home in Grey Highlands is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Grey Highlands holiday home?
Book your Grey Highlands holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Grey Highlands?
Prices for holiday homes in Grey Highlands vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Grey Highlands to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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