Guesthouse holiday rentals in Simcoe County
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Top-rated Guesthouses in Simcoe County
Guests agree: These guesthouses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Simcoe County guesthouses
Family-Friendly guesthouses
Guesthouse in Mansfield
4.99 out of 5 average rating, 93 reviewsBrookside Cottage - Charming Rural Getaway Mulmur
29 Dec – 5 Jan
Guesthouse in Tiny
4.74 out of 5 average rating, 68 reviewsGeorgian Bay Cottage - Tiny Beaches
9–16 Jan
Guesthouse in Tiny
4.39 out of 5 average rating, 61 reviewsFamily Beach Cottage
26 Oct – 2 Nov
Guesthouse in Creemore
Creemore/Mansfield 1BR Private Apartment
23–30 May
Guesthouse in Wasaga Beach
4.44 out of 5 average rating, 9 reviewsCozy Studio
21–28 May
Guesthouse in King City
4.67 out of 5 average rating, 3 reviewsRuby Room
26 Nov – 3 Dec
Guesthouse in Wasaga Beach
4.89 out of 5 average rating, 100 reviews2 -Sun Angel Court Couples Cabin 2
29 Mar – 5 Apr
Guesthouse in Wasaga Beach
4.89 out of 5 average rating, 82 reviews6-Sun Angel Court Cabin 6
21–28 Feb
Guesthouses with a patio
Guesthouse in Shanty Bay
4.99 out of 5 average rating, 88 reviewsThe Guest House, Maplewood Hills
22–29 May
Guesthouse in Barrie
4.5 out of 5 average rating, 10 reviewsLakeview Suite
10–17 Jul
Guesthouse in Barrie
4.69 out of 5 average rating, 13 reviewsCharming Boathouse on Lake Simcoe
15–22 Nov
Guesthouse in Mulmur
5.0 out of 5 average rating, 38 reviewsThe Mulmur Loft
16–23 Nov
Guesthouse in Barrie
5.0 out of 5 average rating, 43 reviewsCentrally Located 2 bedroom Hidden Gem
4–11 Mar
Guesthouse in Barrie
4.98 out of 5 average rating, 41 reviewsRustic luxury chalet with pool, near lake & beach
5–12 Mar
Guesthouse in Georgina
4.71 out of 5 average rating, 51 reviewsFantastic Lake Simcoe Guest House for GTA get-away
7–14 Jan
Guesthouse in Caledon
4.84 out of 5 average rating, 32 reviewsCaledon rural apartment with hot tub and pool
5–12 Oct
Guest house rentals with a washing machine and dryer
Guesthouse in Innisfil
4.87 out of 5 average rating, 53 reviewsThe Refuge Guesthouse - 1 bedroom w/fireplace
8–15 Apr
Guesthouse in Barrie
4.86 out of 5 average rating, 71 reviews2BR cozy Apt close to dwtn, forests, hospital, hwy
8–15 Jun
Guesthouse in Bond Head
4.96 out of 5 average rating, 23 reviewsPrivate Country Guesthouse
15–22 Aug
Guesthouse in Newmarket
4.82 out of 5 average rating, 85 reviewsStylish, Spacious, Clean & New. Perfect Location
28 Aug – 4 Sep
Guesthouse in Collingwood
5.0 out of 5 average rating, 8 reviewsBriar Cottage
12–19 Sep
Guesthouse in Orillia
5.0 out of 5 average rating, 5 reviewsWoods Bay Cottage Severn
12–19 Jul
Guesthouse in Barrie
5.0 out of 5 average rating, 69 reviewsCozy Lakehouse with Views of the Water
26 Dec – 2 Jan
Guesthouse in Wasaga Beach
5.0 out of 5 average rating, 5 reviewsCute 2-bedroom cottage with trailer that sleeps 16
7–14 Jun
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