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Guesthouse vacation rentals in Lake Simcoe

Find and book unique guesthouse rentals on Airbnb

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Popular amenities for Lake Simcoe guesthouses

Family-friendly guesthouses

Guest favourite
Private room in Toronto
4.93 out of 5 average rating, 30 reviews

Private Guesthouse with Sauna

DarylRating, 5 stars1 month ago
It was an amazing stay. The location was quiet and peaceful yet close to everything I needed. The bed was truly, amazingly comfortable! Shelley was a gracious, friendly and helpful host.
Guest favourite
Guesthouse in Bala
4.95 out of 5 average rating, 37 reviews

The Boathouse on Sunset Bay Muskoka

KaraRating, 5 stars8 months ago
Lyn and Peter were amazing hosts for our family of 4 (two adults plus two kids, ages 9&6.) Lyn greeted us at check-in, but gave us privacy after that, and was super quick to respond to texts on the rare occasion we had a question. The boathouse was as described with even more amenities than listed and more spacious and beautiful than the pictures could do justice. The place is immaculate with careful thought and detail into every little decoration and little touches (e.g. a basket in the bedroom with bug spray, package toothbrush, etc. for any forgotten items.) We felt completely at home in the boathouse and enjoyed the beautiful views from the upstairs deck and dock, where we spent the majority of our time. We all loved taking out the SUPs that were there for our use and it was a quick drive into town to visit Don’s Bakery (IYKYK), Splash Island, and the ski show on Tuesday night. Highly recommend the boathouse for your next Muskoka stay! Lyn’s hospitality is 10/10.
Private room in Markham
4.82 out of 5 average rating, 74 reviews

friendly house

TomRating, 5 stars62 months ago
Very friendly, even helped me find my keys. I will stay there again.
Guest favourite
Guesthouse in Toronto
4.91 out of 5 average rating, 150 reviews

Cozy & Bright Private Suite in Trinity Bellwoods

KaseyRating, 5 stars1 week ago
A wonderful stay away from home! For being such a central and bustling neighbourhood, Amanda’s spot was extremely quiet and private which was just what we needed. Thanks for everything!
Guest favourite
Guesthouse in Orangeville
4.95 out of 5 average rating, 351 reviews

Sunny Pines Farm Studio Tennis Court/Bruce Trail

AlexRating, 5 stars2 weeks ago
What a gorgeous place to get away from the city for a few days. The comfortable studio has everything you'd need during your stay. The fields are great for walking (especially if you have a dog), and there are all kinds of magnificent hiking trails nearby. My arrival coincided with a massive ice storm and Vince and Miranda were in touch every step of the way, keeping me updated on conditions and options. They were a pleasure to deal with. I look forward to returning next time I need a taste of the country.
Superhost
Guesthouse in Port Hope
4.92 out of 5 average rating, 63 reviews

haute goat farm | unique alpaca cabin

MelissaRating, 5 stars6 months ago
This farm is incredibly well maintained, the animals seem so happy, and doing the morning chores was not a chore at all - was an awesome, unique experience. The cabin was cozy and super clean, as were the shared washrooms. All staff and volunteers are welcoming, polite and helpful. Debbie herself was a delight! The Screaming Goat Cafe had great selection and the food was delicious! It was lovely to unwind, bond with the animals, and stargaze; and we're looking forward to returning next year to try out one of their Yomes [yurt+dome]!
Guest favourite
Guesthouse in Stoney Lake
4.8 out of 5 average rating, 10 reviews

Cottage suite, lakeside with beautiful view!

Vicki Rating, 5 stars7 months ago
The views and the lake were absolutely beautiful. The rooms were well maintained and comfortable for the age of the Inn with everything you need. Patti and Dennis were delighted and awesome hosts who live on site at the inn and were gracious enough to take guests out on their pontoon boat to tour the lake and some of the 1100 islands.
Guesthouse in Tiny
4.39 out of 5 average rating, 61 reviews

Family Beach Cottage

MarlenaRating, 5 stars19 months ago
We all really enjoyed the cottage! Thank you, Vess, for such a wonderful space.

Guesthouses with a patio

Superhost
Guesthouse in Cobourg
4.88 out of 5 average rating, 17 reviews

The Wilkins - Coach House

ArleneRating, 5 stars1 month ago
Gorgeous property, the only thing I missed was a hairdryer in the bathroom. everything else was brand new and it was stunningly furnished. beautiful space to stay in.
Guest favourite
Guesthouse in CA
4.91 out of 5 average rating, 23 reviews

Adorable GH in beautiful Claremont/scenic view

MalcolmRating, 5 stars13 months ago
Christine was a very helpful host, she was communicative and checked in regularly during my long term stay to ensure I had everything I needed.
Top guest favourite
Guesthouse in Fergus
5 out of 5 average rating, 19 reviews

Millcreek Riverfront Retreat Elora/Fergus

BrendanRating, 5 stars2 months ago
Amy was a great host. The place was very clean when we arrived and even with a snow storm all the paths were kept clear. Everything was fantastic. I would definitely stay here again.
Guest favourite
Guesthouse in Midland
4.92 out of 5 average rating, 12 reviews

Windfall Cottage On Little Lake

AstridRating, 5 stars7 months ago
Windfall Cottage is a unique experience. The cottage is very cozy and tastefully decorated and we felt very comfortable and welcome. The beds are very comfortable, the kitchen perfectly equipped and it is like coming home. The access to the lake and the sun deck with two kayaks are another highlight. Carol and Jonathan are wonderful hosts! The contact was consistently very fast, very friendly and above all very personal. Our inquiry as to whether the cottage was suitable for a wheelchair user was not only answered comprehensively and with further information, but the necessary aids were also provided. Such courteous support is unique and impressive. Windfall Cottage, Carol and Jonathan will remain in our best memories and we can only warmly recommend this Airbnb. Thank you so much for this wonderful experience!
Top guest favourite
Guesthouse in Uxbridge
4.98 out of 5 average rating, 50 reviews

Private Guest House Retreat

CarolineRating, 5 stars2 weeks ago
We had the most magical stay at Victoria's place. From the moment we arrived, it was clear that our host had thought of everything. The cabin was warm and inviting, with soft lighting, a gas fireplace, and comfy throws that made it feel like home right away.  And the hot tub was amazing! To make it even more special, Victoria had decorated the place for my boyfriend's birthday—it was such a sweet surprise for him and really made the weekend feel extra memorable. The kitchen was fully stocked with thoughtful extras like coffee and breakfast bars. The bed was super comfortable and cozy. Victoria was super responsive and so sweet! We learnt we grew up in the same part of N.Ireland and shared a lovely conversation about that.  Little details like the robes and cozy slippers, made us feel like we were at a weekend spa. Whether you're after a peaceful solo retreat or a romantic escape, this cabin is pure winter perfection!
Guest favourite
Guesthouse in Tiny
5 out of 5 average rating, 11 reviews

The Cottage

ahmedRating, 5 stars2 months ago
The place was a home away from home. It was cozy, and the hosts were kind enough to plow the snow as well. Definitely recommended for families.
Guest favourite
Guesthouse in Pickering
4.93 out of 5 average rating, 27 reviews

Spacious fully private studio basement & parking

HariRating, 5 stars4 months ago
Soulmaz’s place is one of the best in town in a safest neighborhood which makes you feel at home. This little studio with adequate space is a perfect place to unwind and spend your time in peace. If you are looking for a home away from home with all amenities to stay, you will definitely enjoy this place. What stands out in this unit is the carefully thought out personalization for any traveller or tourist who wants to relax and settle down. I wish I could have stayed longer and enjoyed the quiet and great atmosphere around this place. I am definitely staying here the next time when I am in this part of town. Thanks Soulmaz for the warm welcome and comfortable place!
Top guest favourite
Guesthouse in Orangeville
5 out of 5 average rating, 46 reviews

Island Lake Guest House

DerekRating, 5 stars1 month ago
This my third time staying at Pam & Andrew’s. That should say enough about how much I like their bunkie. Couldn’t ask for a better stay. Everything as described, beautiful setting and only minutes to town.

Guesthouse rentals with a washer and dryer

Guest favourite
Guesthouse in Markham
4.87 out of 5 average rating, 45 reviews

2 bedroom Guest house in North of Toronto

StuartRating, 5 stars1 week ago
Felt right at home, would not hesitate to book again
Guest favourite
Guesthouse in Richmond Hill
4.97 out of 5 average rating, 68 reviews

"Modern Urban Studio Retreat"

AbidRating, 5 stars1 day ago
This is an exceptional property, offering a cozy and comfortable stay. The host is remarkable, providing helpful and highly accommodating service to ensure guest satisfaction.
Guest favourite
Guesthouse in Toronto
4.96 out of 5 average rating, 67 reviews

Newly Built, One-Bedroom Stylish Apartment

DavidRating, 5 stars8 months ago
We loved everything about staying at Laura’s. She was a great host and very responsive and attentive. We did not need for anything during our stay. We can’t wait to stay here again!
Top guest favourite
Guesthouse in Newmarket
5 out of 5 average rating, 72 reviews

Fairytale - Spotlessly Clean Getaway - 2 Bedroom

AliciaRating, 5 stars3 months ago
You will not regret staying here! I spent 6 weeks here while waiting to move into my own place and I really didn't want to leave. place was spotless, inside and out; it's everything described and more! Alex and his wife are lovely people, he responds almost immediately, very accommodating, and helpful! will definitely be staying here again whenever I visit ontario! Thank you Alex for making me feel at home!
Top guest favourite
Guesthouse in Barrie
4.99 out of 5 average rating, 159 reviews

Warnica Coach House

PeytonRating, 5 stars5 days ago
Beautiful place easy to find and looks exactly like the pictures.
Superhost
Guesthouse in Richmond Hill
5 out of 5 average rating, 3 reviews

Charming Cozy Studio w/ Private Entrance & Parking

RudiRating, 5 stars1 month ago
Really enjoyed my stay, clean and friendly service. Woyld definitely book here again.
Guest favourite
Guesthouse in Richmond Hill
5 out of 5 average rating, 5 reviews

Cozy Studio with Private Entrance & Parking

VictoriaRating, 5 stars2 months ago
Quiet and safe neighbourhood about 35 minutes from city centre with a nice walking path around a pond nearby. Lots of really good restaurants and grocery nearby. Medium sized fenced in yard great for dogs. Clearly marked smoking area. Large driveway spot for car fits SUV. Place was exactly what you expect from the photos - small, but it’s enough space for one person. Host is extremely responsive and helpful. Recommended if you are looking for hassle-free! Tip: there are no bedsheets provided so bring your own double sized. Great stay. Thank you!
Superhost
Guesthouse in Ajax
4.6 out of 5 average rating, 25 reviews

Luxury 2 Bedroom 2 Washroom Legal basement Apart

RenataRating, 5 stars3 months ago
The house is wonderful ,everything very clean of very good taste , I would definitely come back and super recommend !!!

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