Guesthouse vacation rentals in Simcoe County

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Popular amenities for Simcoe County guesthouse rentals

Family-friendly guest house rentals

Guest favorite
Guesthouse in Wasaga Beach
4.85 out of 5 average rating, 100 reviews

3 Sun Angel Court, large family cabin 3

SunilRating, 5 stars10 months ago
overall good experience. 🙏
Superhost
Guesthouse in Wasaga Beach
4.83 out of 5 average rating, 58 reviews

1 - Sun Angel Court. Friends and Family Cabin 1

JasonRating, 5 stars11 months ago
Thank you for making us feel right at home! Really enjoyed our stay.
Superhost
Guesthouse in Wasaga Beach
4.88 out of 5 average rating, 88 reviews

6-Sun Angel Court Cabin 6

JenniferRating, 5 stars10 months ago
Licinia is a wonderful host and went above and beyond to make me feel welcome. The cabin was as described. The deck overlooking the river is relaxing and a great place to chill out. The location is quite close to the Wasaga triathlon so a good spot for participants.
Guest favorite
Guesthouse in Wasaga Beach
4.88 out of 5 average rating, 92 reviews

5- Sun Angel Court (pretty cabin 5)

DiliRating, 5 stars9 months ago
Licinia’s place was amazing. Located super close to the beach, clean, peaceful with a water view and fireplace. She is also very friendly and gave us some recommendations and tips to make the best out of our stay. We will come back!
Superhost
Guesthouse in Wasaga Beach
4.85 out of 5 average rating, 95 reviews

7-SUN ANGEL COURT, LARGE COUPLES CABIN 7

WendyRating, 5 stars9 months ago
Licinia was the perfect hostess. She was pleasant and friendly, making sure our needs were met. At the same time, she gave us our privacy. We thoroughly enjoyed eating the picnic lunch that we brought, sitting on the dock alongside the Nottawasaga River. - entertained by the geese and the ducks, as well as the various watercraft. The beach was just a short walk across the street in the opposite direction of the river. Although it was too windy to swim, the crashing of the waves was a wonderful sound to hear. The cabin was cute and cozy - all the space that we needed. We enjoyed using the gas bbq on site for dinner - there was even an outdoor cook sink and prep area. Our evening was topped off with a bonfire afterwards. We don’t live far from the Town of Wasaga Beach, but we thoroughly enjoyed our weekend getaway and will most definitely return. We look forward to seeing Licinia and her lovely family again.
Guesthouse in Wasaga Beach
4.44 out of 5 average rating, 9 reviews

Cozy Studio

LaurenRating, 5 stars51 months ago
Amazing place!!! Went here for a anniversary and it is close to a lot of things and Anne is very helpful!
Guesthouse in Tiny
4.73 out of 5 average rating, 70 reviews

Georgian Bay Cottage - Tiny Beaches

LisaRating, 5 stars10 months ago
Yaro was an exceptional host! Always quick with his responses. The place is a shared lot but we always felt comfortable and had our privacy at all times.
Superhost
Guesthouse in Wasaga Beach
4.81 out of 5 average rating, 85 reviews

Sun Angel Crt (pretty cabin 9)

FredericRating, 5 stars11 months ago
Perfect place while cyclotouring the area, had a dinner on the beach looking at the sunset. Licinia is a great host, looking for your best stay.

Guest house rentals with a patio

Top guest favorite
Guesthouse in Mono
4.89 out of 5 average rating, 36 reviews

Mono Countryside Home & Farm

JoeRating, 5 stars1 month ago
absolute perfect spot for doing a chunk of the Bruce Trail would be a good base camp for all of the Dufferin Hi—Lands and deep into the Blue Mountain Section. So many good restaurants around.For after your hike, this place feels off the beaten path, and is literally just 1 km from the trail!
Guest favorite
Guesthouse in CA
4.92 out of 5 average rating, 24 reviews

Adorable GH in beautiful Claremont/scenic view

StephanieRating, 5 stars1 month ago
What a wonderful place! They had everything I needed, and it was so lovely and charming. It really felt like home! Plus, it’s conveniently close to all the surrounding towns.
Guest favorite
Guesthouse in Aurora
4.91 out of 5 average rating, 23 reviews

Delightful One-Bedroom Unit Aurora W/ free Parking

YuRating, 5 stars1 month ago
If you are visiting Aurora or even northern Markham / Richman hill, this is a great spot to stay. Very clean, quiet and close to everything. Hooman is very nice to communicate with, made everything go smoothly.
Top guest favorite
Guesthouse in Midland
4.94 out of 5 average rating, 16 reviews

Windfall Cottage On Little Lake

BeeRating, 5 starstoday
Jonathan and Carol were incredibly friendly and welcoming. They greeted us in person, gave us a tour of the cottage, and made us feel right at home. The place itself was stunning—clean, cozy, and beautifully set with the lake just steps from the backyard. Such a peaceful and scenic spot. We absolutely loved our stay and would definitely come back again!
Top guest favorite
Guesthouse in Uxbridge
4.98 out of 5 average rating, 54 reviews

Private Guest House Retreat

PoojaRating, 5 stars1 week ago
Victoria saved us last minute when our previous host stopped responding when we were at the property trying to check in. We found Victoria’s spot last minute and within minutes, she responded to ask us if needed anything additional during our stay. We were at her place 30 minutes later and it was spotless and exactly how the pictures look! I cannot thank Victoria enough for her hospitality and I definitely recommend her place if you’re considering booking it!
Guesthouse in Wasaga Beach
4.76 out of 5 average rating, 25 reviews

Adorable 2 Bedroom guest house with fire place.

Angelica MarcelaRating, 5 stars8 months ago
We enjoyed our stay very much. The cottage had everything we required. The location was perfect for what we wanted. Yousef and Dirk (the complex’s manager) were very kind and easy going and they answered any questions we had. We would love to come back in the summer time.
Guest favorite
Guesthouse in Tiny
4.94 out of 5 average rating, 17 reviews

The Cottage

KyleRating, 5 stars5 days ago
We absolutely loved the cottage! It was perfect for our family of four. We loved being able to walk to the beach in under five minutes. Josh gave us great recommendations during our stay. We hope to come back soon!
Guesthouse in Wasaga Beach
5 out of 5 average rating, 5 reviews

Cute 2-bdrm cottage & trailer that sleeps 16 total

IdaRating, 5 stars23 months ago
Our extended family had a wonderful weekend get together and we want to thank Dirk and Linda for accommodating us! The kids especially loved the novelty of sleeping in the trailer while the adults enjoyed the campfire at night! The cottage is very homey and had everything you need. We will definitely come back and stay longer next time!

Guest house rentals with a washer and dryer

Top guest favorite
Guesthouse in Orillia
5 out of 5 average rating, 27 reviews

Woods Bay Cottage Severn

RuthRating, 5 stars1 week ago
Lovely quiet location, easy to get to. Thank you for looking after us so well. Enjoyed bikes and basketball !
Guesthouse in Collingwood
4.73 out of 5 average rating, 89 reviews

Lovely 2 beds w/Park view, Steps to Harbour front

RashmiRating, 5 stars1 month ago
Guys!! If its Collingwood and you came across this place. Just go for it. My family and I had the most peaceful stay here. Clean place, close to restaurants, and almost everything. Viet, the host is very responsive and addressed every question i had. We plan to go back in summers. It's the perfect spot and one of the best airbnb locations. Vibe check - YES!!. Thanks for hosting us Viet!! See you soon.
Guest favorite
Guesthouse in Georgina
4.95 out of 5 average rating, 40 reviews

Bright & Modern Lower Level Apt in Keswick

EmilyRating, 5 stars2 weeks ago
We had a wonderful stay! Extremely clean, comfortable and spacious. Fully equipped kitchen with everything you would need. Very responsive host. Highly recommend!
Guesthouse in Newmarket
5 out of 5 average rating, 3 reviews

Spacious Airy Central Guesthome

TerrilynnRating, 5 stars2 months ago
Benjamin was an amazing host! He was very responsive to my inquiries, able to accommodate the last minute booking, and provided a “home away from home “ experience. We needed the space after loosing power to our home after a major storm and couldn’t have ended up anywhere better suited. We felt safe in the immaculately clean, warm, and inviting unit and will definitely be recommending the listing to others in the future.
Top guest favorite
Guesthouse in Barrie
4.9 out of 5 average rating, 97 reviews

2BR cozy Apt close to dwtn, forests, hospital, hwy

EmiliaRating, 5 stars3 weeks ago
Nicole’s place is vey cozy and fully equipped with all amenities (in good conditions) to hace a great stay. My family and myself really enjoyed this place, not only for the cleanliness, but also the location in north Barrie. We would definitely stay there again in the next trip to Barrie. Highly recommended!
Superhost
Guesthouse in Newmarket
4.7 out of 5 average rating, 23 reviews

Tranquil Spacious Unit

JulieRating, 5 stars2 weeks ago
I really enjoyed my stay it was nice and quiet and a good area lots of stores around I would definitely stay here again and recommend it and the price is right.
Guesthouse in Georgina
4.73 out of 5 average rating, 15 reviews

Cozy, Sunlight, Lower-Level “Legal Apartment”

AdamRating, 5 stars4 days ago
The place was great, and the host was perfect. Very comfortable stay, and easy to self check in! Suite was clean and nicely decorated. Thank you Maryam
Top guest favorite
Guesthouse in Midland
5 out of 5 average rating, 9 reviews

Hillside Studio: Small Town Escape + Scenic Views

NathanRating, 5 stars1 week ago
Erica is an awesome host and was very accomodating! She was very responsive and had some great recommendations of things to see and do in the area. The studio is super modern and has everything you need for your visit to Midland. It's walking distance to downtown Midland and the Marina.

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