Vacation Rentals in Grey Highlands: 900+ properties

Choose from 947 vacation rentals located in Grey Highlands, Ontario. Top filters in Grey Highlands include Kitchen / Kitchenette, Air conditioner, and Internet / Wifi. Prices range from $39 to $6,989 per night. Our most popular vacation rental types near Grey Highlands are House and Hotel.

Top vacation rentals in Grey Highlands

5.0

Outstanding(264 Reviews)

Condo

in The Blue Mountains

Slope Side Chalet Inspired Townhome , renovated and very clean. Free Night stay.

6 guests · 2 bedrooms · 2 baths

Ski in / Ski out · Garden · Pool

Discover the beauty of Grey Highlands with a stay at Slope Side Chalet Inspired Townhome , renovated and very clean. Free Night stay., a top rated Condo with amenities such as Air conditioner, Dishwasher and Fireplace, and more.

$$$$

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4.8

Outstanding(248 Reviews)

Condo

in The Blue Mountains

Fabulous 2 Level, 2 Bedroom Condo on Blue Mountain! Over 200 ⭐⭐⭐⭐⭐ Reviews!

6 guests · 2 bedrooms · 2 baths

Ski in / Ski out · Pool · Kitchen / Kitchenette

This Condo for $127 in Grey Highlands, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$

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3.6

Good(829 Reviews)

Hotel

in Collingwood

2star

Comfort Inn & Suites

Kitchen / Kitchenette · Air conditioner · Internet / Wifi

Looking for the perfect place to call home during your trip to Grey Highlands? This Hotel offers a comfort and style with top-notch amenities, including Air conditioner, Internet / Wifi and Laundry, and more.

$$$$

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4.5

Excellent(71 Reviews)

Condo

in Blue Mountains

Beautiful & Bright 3 Bed Townhome Near Village

Pool · Pets allowed · Kitchen / Kitchenette

This Condo for $255 in Grey Highlands, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$

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Explore vacation rentals with the most popular amenities in Grey Highlands

Vacation rentals with a kitchen in Grey Highlands

4.9

Outstanding(160 Reviews)

Condo

in The Blue Mountains

✨Pet friendly, ground floor condo, steps to the Village✨

8 guests · 3 bedrooms · 2 baths

Garden · Pool · Pets allowed

Experience vacation in Grey Highlands with our Condo, ✨Pet friendly, ground floor condo, steps to the Village✨. Enjoy amenities such as Air conditioner, Dishwasher and Fireplace, and more.

$$$$

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Living room | TV, fireplace, DVD player, table tennis

4.7

Outstanding(157 Reviews)

Chalet

in Blue Mountains

Beautiful Chalet with Deluxe Hot Tub and Sauna

18 guests · 7 bedrooms · 2 baths

Garden · Pets allowed · Kitchen / Kitchenette

Soak up the beauty of Grey Highlands in our Chalet, Beautiful Chalet with Deluxe Hot Tub and Sauna. With a range of amenities such as Air conditioner, Dishwasher and Fireplace, you'll feel right at home.

$$$$

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3.8

Good(1,089 Reviews)

Resort

in Collingwood

Living Stone Golf Resort

Garden · Pool · Pets allowed

This Resort in Grey Highlands, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

$$$$

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4.1

Excellent(762 Reviews)

Hotel

in Blue Mountains

4star

The Westin Trillium House, Blue Mountain

Ski in / Ski out · Garden · Pool

Looking for a memorable stay in Grey Highlands? Our Hotel might just be what you're looking for. Enjoy amenities including Air conditioner, Dishwasher and Fireplace, and more during your stay.

$$$$

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Grey Highlands

Grey Highlands travel guide

Let us help you plan your perfect Grey Highlands vacation. Our travel guide highlights things to do, places to see, favorite vacation rental amenities in Grey Highlands, and more.