House vacation 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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Grey Highlands house rentals
House rentals with a pool
Home in Owen Sound
4.98 out of 5 average rating, 214 reviewsThe Butchart Estate: your perfect family retreat!
Nov 10 – 17
Home in Chatsworth
4.88 out of 5 average rating, 130 reviewsStonehaven - large country retreat, with pool*
Jan 8 – 15
Home in Collingwood
5.0 out of 5 average rating, 23 reviewsAn oasis getaway near trails, lake, restaurants
May 27 – Jun 3
Home in Flesherton
4.85 out of 5 average rating, 13 reviewsPaul’s Pool House
Nov 25 – Dec 2
Home in The Blue Mountains
5.0 out of 5 average rating, 12 reviewsSpacious Condo next to The Blue Mountains w/ Patio
Nov 14 – 21
Home in Meaford
5.0 out of 5 average rating, 33 reviewsPlume- Guest house
Jan 17 – 24
Home in Collingwood
4.84 out of 5 average rating, 32 reviewsBatteaux Chalet - Pool + Blue Mountain Skiing
Sep 24 – Oct 1
Home in Markdale
5.0 out of 5 average rating, 5 reviewsFarmhouse Retreat - Pool, Sports And Fun, Sleeps 8
Sep 14 – 21
Weekly house rentals
Home in Flesherton
5.0 out of 5 average rating, 13 reviewsEugenia escape
Oct 1 – 8
Home in Collingwood
4.97 out of 5 average rating, 33 reviewsElegant Home in Collingwood -15 min from Village
Oct 6 – 13
Home in Markdale
4.91 out of 5 average rating, 77 reviewsSpacious Cottage - Enjoy the Trails!
May 23 – 30
Home in Collingwood
4.94 out of 5 average rating, 80 reviewsPrivate, brand-new 1 bdrm unit
Aug 31 – Sep 7
Home in Williamsford
4.96 out of 5 average rating, 24 reviewsWilliamsford Blacksmith Shop
Dec 18 – 25
Home in Creemore
4.95 out of 5 average rating, 22 reviewsThe Burrow - 240 Acre Farm with Private Waterfall
Jun 8 – 15
Home in Meaford
4.97 out of 5 average rating, 32 reviewsNewly renovated century home
Dec 22 – 29
Home in Markdale
5.0 out of 5 average rating, 23 reviewsBlue Heron Acres
May 30 – Jun 6
Private house rentals
Home in Meaford
5.0 out of 5 average rating, 12 reviewsCharming Red Brick Home in Meaford ON
Aug 6 – 13
Home in Shallow Lake
4.97 out of 5 average rating, 64 reviewsHindman House: Historic, restful, fully-equipped
Apr 12 – 19
Home in Markdale
5.0 out of 5 average rating, 46 reviewsThe Berkeley-Perfect Four Season Getaway
Jun 21 – 28
Home in Collingwood
4.89 out of 5 average rating, 18 reviewsThe Collingwood House - spacious home near slopes
Apr 18 – 25
Home in Collingwood
5.0 out of 5 average rating, 17 reviewsCharming Townhome in Collingwood
Mar 13 – 20
Home in Collingwood
4.86 out of 5 average rating, 28 reviewsQuaint cottage with local beach
May 8 – 15
Home in South Bruce Peninsula
4.89 out of 5 average rating, 19 reviewsPine Villa-Mediterranean Cottage
Sep 30 – Oct 7
Home in Meaford
4.97 out of 5 average rating, 68 reviewsBirdsong, the perfect Blue Mountains getaway
Nov 12 – 19
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
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