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Guesthouse holiday 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 stars2 months 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 stars9 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 stars63 months ago
Very friendly, even helped me find my keys. I will stay there again.
Top Guest favourite
Guesthouse in Algonquin Highlands
4.93 out of 5 average rating, 152 reviews

Charming mini-cottage, footsteps to water's edge

JeriRating, 5 stars7 months ago
What a beautiful cottage on a beautiful lake! The multiple windows really let in the outdoors. there were so many different places to sit outside to enjoy nature and the lake. We used a kayak and a canoe, and Catherine provided all the safety equipment too. She even lent us a couple fishing poles. We chose the option to leave $10 for the garbage removal rather than take it to the dump ourselves. Everything was so simple. We are so glad we chose this cottage.
Guest favourite
Guesthouse in Toronto
4.91 out of 5 average rating, 152 reviews

Cozy & Bright Private Suite in Trinity Bellwoods

SarahRating, 5 stars1 week ago
Easy to follow instructions for check in. Lovely little suite. On a really nice road. Friendly hosts. Would recommend and would stay again!
Guest favourite
Guesthouse in Orangeville
4.95 out of 5 average rating, 351 reviews

Sunny Pines Farm Studio Tennis Court/Bruce Trail

AlexRating, 5 stars1 month 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 stars7 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
4.82 out of 5 average rating, 11 reviews

Cottage suite, lakeside with beautiful view!

ShradhaRating, 5 stars2 weeks ago
Patricia & Dennis were amazing hosts and very accommodating. The loft was great with an amazing view and balcony to enjoy the weather. They were very kind and helpful. It’s a great place to enjoy and relax ..!!!

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, 20 reviews

Millcreek Riverfront Retreat Elora/Fergus

ShaunaRating, 5 stars1 week ago
This was a truly serene and tranquil place. Close to town. The walkway with the running water was beautiful and it was great to have my morning coffee while sitting on the porch looking over the river.
Guest favourite
Guesthouse in Midland
4.92 out of 5 average rating, 12 reviews

Windfall Cottage On Little Lake

AstridRating, 5 stars8 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, 51 reviews

Private Guest House Retreat

CarolineRating, 5 stars1 month 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!
Top Guest favourite
Guesthouse in Elora
5 out of 5 average rating, 40 reviews

Carriage House - Elora

TaraRating, 5 stars2 days ago
This place was such a wonderful spot in Elora! The property was so cute and the accommodations were perfect for a little getaway! Highly recommend!
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!

Guest house rentals with a washing machine and dryer

Guest favourite
Guesthouse in Markham
4.87 out of 5 average rating, 47 reviews

2 bedroom Guest house in North of Toronto

BarbaraRating, 5 stars1 day ago
Great host, really kind and very quick responses!!
Top Guest favourite
Guesthouse in Richmond Hill
4.97 out of 5 average rating, 72 reviews

"Modern Urban Studio Retreat"

KristianRating, 5 stars1 week ago
Thanks for the wonderful stay. We had a very good time on site. The apartment is small but still very cozy and therefore definitely recommended. It was very clean. The communication was easy and straightforward.
Top Guest favourite
Guesthouse in Newmarket
5 out of 5 average rating, 72 reviews

Fairytale - Spotlessly Clean Getaway - 2 Bedroom

AliciaRating, 5 stars4 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, 161 reviews

Warnica Coach House

RichardRating, 5 stars1 week ago
My wife and I had a great stay. They thought of everything. So comfortable and private. Walking distance to downtown Barrie and the waterfront. Great stay! We will be returning.
Superhost
Guesthouse in Richmond Hill
5 out of 5 average rating, 4 reviews

Charming Cozy Studio w/ Private Entrance & Parking

RudiRating, 5 stars2 months 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, 7 reviews

Cozy Studio with Private Entrance

IrynaRating, 5 stars1 week ago
Nojan was a great host, very responsive.
Superhost
Guesthouse in Ajax
4.6 out of 5 average rating, 25 reviews

Luxury 2 Bedroom 2 Washroom Legal basement Apart

RenataRating, 5 stars4 months ago
The house is wonderful ,everything very clean of very good taste , I would definitely come back and super recommend !!!
Top Guest favourite
Guesthouse in Port Perry
4.97 out of 5 average rating, 70 reviews

Port Perry Island Krazee Acres Hobby Farm

MaddieRating, 5 stars2 weeks ago
My stay here was nothing short of perfect, Debbie made us feel right at home and brought us farm fresh eggs when we arrived. The place was clean and beautiful and getting to see the cows was a bonus! We will definitely be back! -Maddie and Ryan

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