Guesthouse vacation rentals in Simcoe County
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Top-rated guesthouse rentals in Simcoe County
Guests agree: these guesthouse rentals 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 Simcoe County guesthouse rentals
Family-friendly guest house rentals
Guesthouse in Mansfield
4.99 out of 5 average rating, 93 reviewsBrookside Cottage - Charming Rural Getaway Mulmur
Dec 31 – Jan 7
Guesthouse in Tiny
4.74 out of 5 average rating, 68 reviewsGeorgian Bay Cottage - Tiny Beaches
Mar 16 – 23
Guesthouse in Tiny
4.39 out of 5 average rating, 61 reviewsFamily Beach Cottage
Sep 14 – 21
Guesthouse in Creemore
Creemore/Mansfield 1BR Private Apartment
May 10 – 17
Guesthouse in Wasaga Beach
4.44 out of 5 average rating, 9 reviewsCozy Studio
May 23 – 30
Guesthouse in King City
4.67 out of 5 average rating, 3 reviewsRuby Room
Mar 25 – Apr 1
Guesthouse in Wasaga Beach
4.89 out of 5 average rating, 100 reviews2 -Sun Angel Court Couples Cabin 2
Apr 15 – 22
Guesthouse in Wasaga Beach
4.89 out of 5 average rating, 82 reviews6-Sun Angel Court Cabin 6
Mar 5 – 12
Guest house rentals with a patio
Guesthouse in Barrie
4.5 out of 5 average rating, 10 reviewsLakeview Suite
Jul 3 – 10
Guesthouse in Shanty Bay
4.99 out of 5 average rating, 88 reviewsThe Guest House, Maplewood Hills
Aug 4 – 11
Guesthouse in Barrie
4.69 out of 5 average rating, 13 reviewsCharming Boathouse on Lake Simcoe
Nov 24 – Dec 1
Guesthouse in Barrie
5.0 out of 5 average rating, 43 reviewsCentrally Located 2 bedroom Hidden Gem
Mar 6 – 13
Guesthouse in Mulmur
5.0 out of 5 average rating, 38 reviewsThe Mulmur Loft
Jan 26 – Feb 2
Guesthouse in Barrie
4.98 out of 5 average rating, 41 reviewsRustic luxury chalet with pool, near lake & beach
Mar 11 – 18
Guesthouse in Georgina
4.71 out of 5 average rating, 51 reviewsFantastic Lake Simcoe Guest House for GTA get-away
Aug 29 – Sep 5
Guesthouse in Caledon
4.84 out of 5 average rating, 32 reviewsCaledon rural apartment with hot tub and pool
Oct 4 – 11
Guest house rentals with a washer and dryer
Guesthouse in Barrie
4.99 out of 5 average rating, 75 reviewsWarnica Coach House
Oct 19 – 26
Guesthouse in Barrie
4.86 out of 5 average rating, 71 reviews2BR cozy Apt close to dwtn, forests, hospital, hwy
Jul 7 – 14
Guesthouse in Bond Head
4.96 out of 5 average rating, 23 reviewsPrivate Country Guesthouse
Sep 10 – 17
Guesthouse in Newmarket
4.82 out of 5 average rating, 85 reviewsStylish, Spacious, Clean & New. Perfect Location
Jul 9 – 16
Guesthouse in Collingwood
5.0 out of 5 average rating, 8 reviewsBriar Cottage
Jun 10 – 17
Guesthouse in Orillia
5.0 out of 5 average rating, 5 reviewsWoods Bay Cottage Severn
Jan 20 – 27
Guesthouse in Barrie
5.0 out of 5 average rating, 69 reviewsCozy Lakehouse with Views of the Water
Feb 4 – 11
Guesthouse in Wasaga Beach
5.0 out of 5 average rating, 5 reviewsCute 2-bedroom cottage with trailer that sleeps 16
May 12 – 19
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