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Guest house holiday rentals in Lake Simcoe

Find and book unique guest house rentals on Airbnb

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Popular amenities for guest house rentals in Lake Simcoe

Family-friendly guest house rentals

Guest favourite
Guest house in Bala
4.95 out of 5 average rating, 37 reviews

The Boathouse on Sunset Bay Muskoka

KaraRating, 5 stars10 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.
Top guest favourite
Guest house in Algonquin Highlands
4.93 out of 5 average rating, 154 reviews

Charming mini-cottage, footsteps to water's edge

VladimirRating, 5 stars2 weeks ago
This cabin offers a cozy retreat. The space is snug and warm—perfect for curling up with a book or simply watching the rain fall through large windows. All of the amenities were as described and we look forward to returning.
Guest favourite
Guest house in Toronto
4.92 out of 5 average rating, 155 reviews

Cozy & Bright Private Suite in Trinity Bellwoods

LizRating, 5 stars5 days ago
Absolutely amazing place Amanda has, the location right next to Bellwoods park is just perfect for those warm evenings. Amanda was an amazing host who gave some really good recommendations for what to do in the Toronto area. Will definitely book again when i’m back in Toronto!
Top guest favourite
Guest house in Toronto
4.93 out of 5 average rating, 313 reviews

Free Parking 2BD Queen St. East

MitchRating, 5 stars1 month 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!
Superhost
Guest house in Port Hope
4.92 out of 5 average rating, 64 reviews

haute goat farm | unique alpaca cabin

MelissaRating, 5 stars8 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
Guest house in Stoney Lake
4.82 out of 5 average rating, 11 reviews

Cottage suite, lakeside with beautiful view!

ShradhaRating, 5 stars1 month 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 ..!!!
Guest house 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!
Guest house 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.

Guest house rentals with a patio

Top guest favourite
Guest house in Fergus
5 out of 5 average rating, 20 reviews

Millcreek Riverfront Retreat Elora/Fergus

ShaunaRating, 5 stars1 month 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
Guest house in Mississauga
4.75 out of 5 average rating, 119 reviews

Luxurious Apartment overlooking Ravin & Pool

JulieRating, 5 stars2 weeks ago
Exactly how it looks. comfy bed with a very nice living room.
Top guest favourite
Guest house in Port Perry
5 out of 5 average rating, 84 reviews

Lakeside Guest Suite, on Lake Scugog, Port Perry

AnureetpalRating, 5 stars4 days ago
We had a really good time, the place is spotless and very cozy. It’s accommodated with everything. The view is beautiful and peaceful. Lydia and Craig are very responsive, friendly and respectful. 10/10 experience and grateful for snacks/haply birthday sign/ carved gift during welcome.
Top guest favourite
Guest house in Innisfil
5 out of 5 average rating, 36 reviews

A Greyt Escape

DelilahRating, 5 stars3 weeks ago
Beautiful quiet stay!! Loved it here, definitely would book again in the future!
Top guest favourite
Guest house in Barrie
4.99 out of 5 average rating, 81 reviews

Rustic luxury chalet near beach with private pool

DanaRating, 5 stars2 weeks ago
We had a great time on our stay here. Just as described, the chalet provides privacy and comfort. The linens on the bed were to die for! Great space for relaxing with a small group and the island is perfect for a games night! They had coffee to get through the mornings and shower essentials as well. We would highly recommend this space for your next trip!
Superhost
Guest house in Annan
4.85 out of 5 average rating, 108 reviews

Lakeview Loft with Hot Tub on Irish Mountain

JeffRating, 5 stars3 days ago
interesting location. Very private for a couples weekend. I would stay again. For a 1 st visitor I suggest being creative with your dining expectations.
Top guest favourite
Guest house in Uxbridge
4.98 out of 5 average rating, 53 reviews

Private Guest House Retreat

KostaRating, 5 stars2 weeks ago
My fiancé and I were in Toronto for the weekend and found Victoria’s spot to book just a bit out of the city. It was the perfect spot to come back to after a busy day. Extremely clean and the hot tub was super relaxing. Will definitely be looking to stay at Victoria’s spot in the future again!
Superhost
Guest house in Barrie
4.62 out of 5 average rating, 21 reviews

Cozy Waterfront Boathouse with Lake Simcoe Views

KatharineRating, 5 stars9 months ago
I had a wonderful stay at the boat house while visiting Barrie for a wedding. The location on the water was absolutely lovely! Bruce was incredibly helpful, providing clear instructions and great suggestions that made settling in a breeze. Coming from Australia, I’m used to pristine beaches, so we chose not to swim in the lake as it didn’t seem very clean. However, we thoroughly enjoyed relaxing by the water. Overall, it was a lovely experience!

Guest house rentals with a washing machine and dryer

Guest favourite
Guest house in Caledon
5 out of 5 average rating, 6 reviews

Cozy Private Ensuite Basement Bedroom

De-VoreRating, 5 stars1 month ago
My parents had a great stay! The place was modern, very clean, and exactly as pictured. You can tell the host really puts effort into maintaining the space — everything felt fresh, comfortable, and welcoming. Check-in was smooth, and communication was easy throughout. I would definitely stay here again and recommend it to anyone looking for a clean, stylish spot.
Superhost
Guest house in Pickering
5 out of 5 average rating, 4 reviews

Romantic Private Guest House

KunalRating, 5 stars5 months ago
Lovely place to stay, clean, comfortable and well equipped, it looks exactly what the images shows and had everything we needed. Saulmaz is really a great host and we really enjoyed our stay here. Would definitely Consider returning to this property for a long stay.
Guest favourite
Guest house in Toronto
5 out of 5 average rating, 26 reviews

Junction Private Laneway Suite with Backyard

PierreRating, 5 stars2 weeks ago
La laneway suite de Kendall est moderne, propre, bien équipée, au calme ; elle est bien située à proximité de bus et tramways à passages fréquents permettant de se déplacer facilement dans toute l'agglomération de Toronto. ll y a le centre commercial Stockyards village juste à coté ainsi que d'autres commerces et points de restauration classique ou rapide. Le logement correspondait tout à fait à notre besoin pour notre séjour de 10jours ; nous espérons le trouver disponible lorsque nous reviendrons à Toronto.
Guest favourite
Guest house in Pickering
4.96 out of 5 average rating, 25 reviews

Frenchman Bay Luxury Basement

AaronRating, 5 stars4 days ago
Huma was so kind and friendly; her warmth made us feel like we were staying with family. The apartment is exceptionally comfortable and clean, with a very nice layout and thoughtful design. The home is easy to access from the highway and located in an ideal spot for exploring the waterfront trails. We enjoyed the bbq and outdoor space, but most of all we appreciated Huma’s amazing hospitality. Thank you, Huma! See you next time! ❤️
Top guest favourite
Guest house in Toronto
5 out of 5 average rating, 28 reviews

My Happy Place - Beaches Apartment

JoelRating, 5 stars6 days ago
Maria was a fantastic host always really responsive and helpful. Check in with smooth and the space itself is great. It’s a basement conversion but even manages to get in a decent amount of light. Loads of thoughtful extras and really well kitted out kitchen! We did hear some noise from upstairs as the soundproofing isn’t great. But overall a really great stay and would recommend if you’re looking for somewhere in the beaches area!
Top guest favourite
Guest house in Meaford
4.96 out of 5 average rating, 26 reviews

The Coach House at Belvedere Farm

AjRating, 5 stars1 week ago
The entire experience was world class. Not only was the coach house one of the most unique & beautiful air bnb's that I have ever stayed in, but the care & kindness of the hosts (Peri and Andrew) made the experience 7, 8, nay, 10 Stars! The space itself floored us. Everything was so intentional and beautiful. The surroundings were serene, the small touches (like homemade pancake mix, local jam, and a bouquet of flowers) were above and beyond. Being pet friendly was a huge benefit for me since I was travelling from the Maritimes with my best buddy Henderson, and they left out everything needed for a persons-best-friend too! All in all, the experience was top notch, and I would encourage anyone looking for a restful retreat to consider Peri & Andrew's unique coach house :)
Superhost
Guest house in Newmarket
4.8 out of 5 average rating, 20 reviews

Tranquil Spacious Unit

JulieRating, 5 stars6 days 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.
Guest favourite
Guest house in Feversham
4.92 out of 5 average rating, 181 reviews

Guesthouse Getaway

RitaRating, 5 stars3 months ago
Beautiful location, with clear directions on how to find. Hosts were flexible and allowed me to check-in early, which I appreciated so much. It snowed while I was there, and they had the driveway and parking area all cleared. The place was clean & cozy - I would stay again!

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