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 29 – Jan 5
Guesthouse in Tiny
4.74 out of 5 average rating, 68 reviewsGeorgian Bay Cottage - Tiny Beaches
Jan 9 – 16
Guesthouse in Tiny
4.39 out of 5 average rating, 61 reviewsFamily Beach Cottage
Oct 26 – Nov 2
Guesthouse in Creemore
Creemore/Mansfield 1BR Private Apartment
May 23 – 30
Guesthouse in Wasaga Beach
4.44 out of 5 average rating, 9 reviewsCozy Studio
May 21 – 28
Guesthouse in King City
4.67 out of 5 average rating, 3 reviewsRuby Room
Nov 26 – Dec 3
Guesthouse in Wasaga Beach
4.89 out of 5 average rating, 100 reviews2 -Sun Angel Court Couples Cabin 2
Mar 29 – Apr 5
Guesthouse in Wasaga Beach
4.89 out of 5 average rating, 82 reviews6-Sun Angel Court Cabin 6
Feb 21 – 28
Guest house rentals with a patio
Guesthouse in Shanty Bay
4.99 out of 5 average rating, 87 reviewsThe Guest House, Maplewood Hills
May 22 – 29
Guesthouse in Barrie
4.5 out of 5 average rating, 10 reviewsLakeview Suite
Jul 10 – 17
Guesthouse in Barrie
4.69 out of 5 average rating, 13 reviewsCharming Boathouse on Lake Simcoe
Nov 15 – 22
Guesthouse in Mulmur
5.0 out of 5 average rating, 38 reviewsThe Mulmur Loft
Nov 16 – 23
Guesthouse in Barrie
5.0 out of 5 average rating, 43 reviewsCentrally Located 2 bedroom Hidden Gem
Mar 4 – 11
Guesthouse in Barrie
4.98 out of 5 average rating, 41 reviewsRustic luxury chalet with pool, near lake & beach
Mar 5 – 12
Guesthouse in Georgina
4.71 out of 5 average rating, 51 reviewsFantastic Lake Simcoe Guest House for GTA get-away
Jan 7 – 14
Guesthouse in Caledon
4.84 out of 5 average rating, 32 reviewsCaledon rural apartment with hot tub and pool
Oct 5 – 12
Guest house rentals with a washer and dryer
Guesthouse in Innisfil
4.87 out of 5 average rating, 53 reviewsThe Refuge Guesthouse - 1 bedroom w/fireplace
Apr 8 – 15
Guesthouse in Barrie
4.86 out of 5 average rating, 71 reviews2BR cozy Apt close to dwtn, forests, hospital, hwy
Jun 8 – 15
Guesthouse in Bond Head
4.96 out of 5 average rating, 23 reviewsPrivate Country Guesthouse
Aug 15 – 22
Guesthouse in Newmarket
4.82 out of 5 average rating, 85 reviewsStylish, Spacious, Clean & New. Perfect Location
Aug 28 – Sep 4
Guesthouse in Collingwood
5.0 out of 5 average rating, 8 reviewsBriar Cottage
Sep 12 – 19
Guesthouse in Orillia
5.0 out of 5 average rating, 5 reviewsWoods Bay Cottage Severn
Jul 12 – 19
Guesthouse in Barrie
5.0 out of 5 average rating, 69 reviewsCozy Lakehouse with Views of the Water
Dec 26 – Jan 2
Guesthouse in Wasaga Beach
5.0 out of 5 average rating, 5 reviewsCute 2-bedroom cottage with trailer that sleeps 16
Jun 7 – 14
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