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