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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
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.
Superhost
Private room in Meaford
5 out of 5 average rating, 3 reviews

Creative Refuge for Artists, Yogis & Nature Lovers

TozhegRating, 5 stars3 months ago
Esther is an amazing host, clear and friendly communication and personable and caring host. Her place is styled in a very beautiful way to create a peaceful and homey experience , very clean and fully equipped. I enjoyed my stay very much and indeed can’t wait to go back and experience this property in different seasons.
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!
Top Guest favourite
Guesthouse in Toronto
4.93 out of 5 average rating, 313 reviews

Free Parking 2BD Queen St. East

MitchRating, 5 stars1 week ago
I had a truly wonderful stay at Branko, Milan, and Bissa’s place, conveniently located in the east end of Toronto. From the moment I arrived, Bissa and Milan made me feel incredibly welcome—like part of the family! They were a joy to chat with whenever our paths crossed, and Branko was always quick and helpful with any questions before and during my stay. The hosts live in the main and basement floors and the second and third floors, accessed through a private entrance, offered more space than expected. It was peaceful, quiet, and perfect for rest after long days. Decorated with plenty of interesting artwork for all tastes. The dedicated parking spot was a huge plus, and I appreciated the hot showers, cozy bedding, soft towels, and fully equipped kitchen and bathroom—everything I needed for a 6-week stay. I’m already looking forward to my next project in Toronto, as their place is high on my list. I would absolutely 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 ..!!!
Guesthouse in Tiny
4.39 out of 5 average rating, 61 reviews

Family Beach Cottage

SolèneRating, 5 stars20 months ago
Nous avons grandement apprécié notre séjour, quelques changements seraient souhaitables pour le rapport qualité prix. Cela ne nous empêchera pas d'y retourner avec plaisir !

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

AnastasiaRating, 5 stars7 months ago
Я проживала в доме 3 недели вместе с младенцем. Christine самый добрый и гостеприимный хозяин из всех - для малыша была подготовлена ванночка, а на день рождения - прекрасные подарки. Дом находится в уединенном месте - обязательно нужна машина. Вокруг поля и чистейший воздух. В доме было все, что нужно для длительного комфортного пребывания, от зубной пасты до средства для мытья полов. Я чувствовала себя как дома. мебель подобрана специально для этого дома: нет никаких старых вещей или полотенец. Особенно важно - это отдельный гостевой дом, а не подвал, как большинство сдаваемого жилья за эту цену. Когда я буду в Торонто еще раз, я непременно буду оставаться только тут.
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.
Superhost
Guesthouse in Mississauga
4.74 out of 5 average rating, 116 reviews

Luxurious Apartment overlooking Ravin & Pool

MariyamRating, 5 stars1 month ago
I had a great stay at Farah's place! The unit was clean and looked exactly like the photos. The host was very friendly and responsive. I would visit again!
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!
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

燕萍Rating, 5 stars2 weeks ago
入住很方便,房子是个walk out basement, 有阳光。楼上总体很安静。厨房用品也很齐全。是个适合一家人的居所。
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
Vielen Dank für den schönen Aufenthalt. Wir hatten eine sehr gute Zeit vor Ort. Die Wohnung ist zwar klein aber dennoch sehr gemütlich und daher auf jeden Fall zu empfehlen. Es war sehr sauber. Die Kommunikation verlief einfach und unkompliziert.
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, 162 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 stars2 weeks 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
A casa é maravilhosa ,tudo muito limpo de de muito bom gosto ,com certeza voltaria e super recomendo !!!
Top Guest favourite
Guesthouse in Port Perry
4.97 out of 5 average rating, 71 reviews

Port Perry Island Krazee Acres Hobby Farm

KorinnRating, 5 stars2 days ago
this was such a wonderful space to be able to escape and relax! thank you for having a comfortable, safe, relaxing, fantasy world cozy space! I need to get me a bathtub like yours! Spent most of my time in that haha. Thanks again for the peaceful comfortable getaway!

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