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 7 – 14
Home in Chatsworth
4.88 out of 5 average rating, 130 reviewsStonehaven - large country retreat, with pool*
Sep 6 – 13
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 22 – 29
Home in The Blue Mountains
5.0 out of 5 average rating, 12 reviewsSpacious Condo next to The Blue Mountains w/ Patio
Apr 20 – 27
Home in Meaford
5.0 out of 5 average rating, 33 reviewsPlume- Guest house
Apr 2 – 9
Home in Collingwood
4.84 out of 5 average rating, 32 reviewsBatteaux Chalet - Pool + Blue Mountain Skiing
Sep 25 – Oct 2
Home in Markdale
5.0 out of 5 average rating, 5 reviewsFarmhouse Retreat - Pool, Sports And Fun, Sleeps 8
Sep 12 – 19
Weekly house rentals
Home in Kimberley
4.89 out of 5 average rating, 66 reviewsRiver and Ridge Retreat
Sep 9 – 16
Home in Markdale
4.91 out of 5 average rating, 77 reviewsSpacious Cottage - Enjoy the Trails!
Jan 18 – 25
Home in Flesherton
5.0 out of 5 average rating, 13 reviewsEugenia escape
Oct 16 – 23
Home in Collingwood
4.94 out of 5 average rating, 79 reviewsPrivate, brand-new 1 bdrm unit
May 8 – 15
Home in Collingwood
4.97 out of 5 average rating, 33 reviewsElegant Home in Collingwood -15 min from Village
Mar 16 – 23
Home in Meaford
4.97 out of 5 average rating, 32 reviewsNewly renovated century home
May 24 – 31
Home in Williamsford
4.96 out of 5 average rating, 23 reviewsWilliamsford Blacksmith Shop
Dec 21 – 28
Home in Creemore
4.95 out of 5 average rating, 22 reviewsThe Burrow - 240 Acre Farm with Private Waterfall
Jun 8 – 15
Private house rentals
Home in Singhampton
5.0 out of 5 average rating, 12 reviews7 acre, 5+ bdrm, Singhampton (Collingwood) Cottage
May 30 – Jun 6
Home in Meaford
5.0 out of 5 average rating, 12 reviewsCharming Red Brick Home in Meaford ON
Jun 20 – 27
Home in Shallow Lake
4.97 out of 5 average rating, 64 reviewsHindman House: Historic, restful, fully-equipped
Apr 10 – 17
Home in Markdale
5.0 out of 5 average rating, 46 reviewsThe Berkeley-Perfect Four Season Getaway
Jul 10 – 17
Home in Collingwood
5.0 out of 5 average rating, 17 reviewsCharming Townhome in Collingwood
Dec 5 – 12
Home in Collingwood
4.9 out of 5 average rating, 21 reviewsBeautiful Family Bungalow in Downtown Collingwood
May 3 – 10
Home in Shelburne
5.0 out of 5 average rating, 15 reviewsTranquil 2BR Triplex in the Heart of Shelburne
Oct 8 – 15
Home in Southgate
5.0 out of 5 average rating, 15 reviewsBeautiful four bedroom house available in Dundalk
Sep 5 – 12
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
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- Family travel hub Tips and inspiration
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- Outdoor adventure Explore nature with the family
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