House holiday rentals in Grey Highlands
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Top-rated house rentals in Grey Highlands
Guests agree: these houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for house rentals in Grey Highlands
House rentals with a pool
Home in Owen Sound
4.98 out of 5 average rating, 214 reviewsThe Butchart Estate: your perfect family retreat!
9–16 Nov
Home in Chatsworth
4.88 out of 5 average rating, 130 reviewsStonehaven - large country retreat, with pool*
8–15 Jan
Home in Collingwood
5.0 out of 5 average rating, 23 reviewsAn oasis getaway near trails, lake, restaurants
27 May – 3 Jun
Home in Flesherton
4.85 out of 5 average rating, 13 reviewsPaul’s Pool House
4–11 Apr
Home in The Blue Mountains
5.0 out of 5 average rating, 12 reviewsSpacious Condo next to The Blue Mountains w/ Patio
24 Apr – 1 May
Home in Meaford
5.0 out of 5 average rating, 33 reviewsPlume- Guest house
15–22 Mar
Home in Collingwood
4.84 out of 5 average rating, 32 reviewsBatteaux Chalet - Pool + Blue Mountain Skiing
19–26 Oct
Home in Markdale
5.0 out of 5 average rating, 5 reviewsFarmhouse Retreat - Pool, Sports And Fun, Sleeps 8
13–20 Sep
Weekly house rentals
Home in Penetanguishene
4.97 out of 5 average rating, 143 reviewsWhite Rolling Sands of Penetang by Theatre
2–9 Jun
Home in Kimberley
4.89 out of 5 average rating, 66 reviewsRiver and Ridge Retreat
24 Apr – 1 May
Home in Markdale
4.91 out of 5 average rating, 77 reviewsSpacious Cottage - Enjoy the Trails!
19–26 Jan
Home in Flesherton
5.0 out of 5 average rating, 13 reviewsEugenia escape
17–24 Oct
Home in Collingwood
4.97 out of 5 average rating, 33 reviewsElegant Home in Collingwood -15 min from Village
7–14 Apr
Home in Collingwood
4.94 out of 5 average rating, 79 reviewsPrivate, brand-new 1 bdrm unit
3–10 Aug
Home in Williamsford
4.96 out of 5 average rating, 23 reviewsWilliamsford Blacksmith Shop
9–16 May
Home in Meaford
4.97 out of 5 average rating, 32 reviewsNewly renovated century home
24 Nov – 1 Dec
Private house rentals
Home in Shallow Lake
4.97 out of 5 average rating, 64 reviewsHindman House: Historic, restful, fully-equipped
11–18 Apr
Home in Collingwood
4.91 out of 5 average rating, 22 reviewsBlue Mountain Home
1–8 Jan
Home in Meaford
5.0 out of 5 average rating, 12 reviewsCharming Red Brick Home in Meaford ON
21–28 Jun
Home in Badjeros
5.0 out of 5 average rating, 32 reviewsJJ’s small town country retreat
21–28 Apr
Home in Markdale
5.0 out of 5 average rating, 46 reviewsThe Berkeley-Perfect Four Season Getaway
23–30 Sep
Home in Shelburne
5.0 out of 5 average rating, 15 reviewsTranquil 2BR Triplex in the Heart of Shelburne
31 Aug – 7 Sep
Home in Collingwood
5.0 out of 5 average rating, 17 reviewsCharming Townhome in Collingwood
6–13 Dec
Home in Hawkestone
4.93 out of 5 average rating, 55 reviewsLakeside Cottage Getaway
24–31 Oct
Quick stats about house rentals in Grey Highlands
Total rentals
290 properties
Rentals with dedicated workspaces
140 properties have a dedicated workspace
Rentals with a pool
50 properties have a pool
Pet-friendly rentals
110 properties allow pets
Family-friendly rentals
250 properties are a good fit for families
Total number of reviews
6K reviews
Destinations to explore
- Brampton Holiday rentals
- Muskoka Lakes Holiday rentals
- Kitchener Holiday rentals
- Waterloo Holiday rentals
- Oakville Holiday rentals
- Barrie Holiday rentals
- Tobermory Holiday rentals
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