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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
Private room in Toronto
4.95 out of 5 average rating, 40 reviews

Private Guesthouse with Sauna

JohnRating, 5 stars3 weeks ago
Everything in this carefully designed duplex coach house is just so. Unlocking the European-style tilt & turn outer door maybe a challenge at first, but it works well. Two large non-representational paintings are pleasing dashes of colour in the main studio bedroom. The loft sauna is very cleverly designed and easy to use. The passageway to access the backyard and the suite is as little as 22-inches wide at a couple of points, which may be difficult for some people and luggage to traverse. But it's worth the squeeze!
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.
Guest favourite
Guest house in Toronto
4.92 out of 5 average rating, 155 reviews

Cozy & Bright Private Suite in Trinity Bellwoods

LizRating, 5 stars2 weeks 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, 314 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 stars2 months 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, 21 reviews

Millcreek Riverfront Retreat Elora/Fergus

SarahRating, 5 stars6 days ago
We had a fantastic stay at the Millcreek Retreat! The location was beautiful, it felt completely private and had gorgeous views over the river from the balcony and bedroom. The place was spotless and had everything that we could have needed during our stay. Would recommend this Airbnb to anyone and everyone! It was the perfect location for our little babymoon getaway.
Superhost
Guest house in Mississauga
4.75 out of 5 average rating, 120 reviews

Luxurious Apartment overlooking Ravin & Pool

MahmoudRating, 5 stars1 week ago
We had a wonderful stay at Farah's house! Everything was clean, organized, and very welcoming. The view from the windows was truly the highlight. Farah and her family were incredibly kind and helpful — whenever we had any questions or issues, they responded within minutes and provided the support we needed. They even kindly offered to help us with laundry, which we really appreciated. 😊 The neighborhood is lovely, with a great park just a three-minute walk from the house. If I had to mention one small downside, it would be a slight smell in the living room. It wasn’t strong and didn’t affect our stay, and honestly, I’m sure Farah would’ve taken care of it if we’d mentioned it — but it wasn’t a big deal. We still really enjoyed spending time there, especially in front of the big screen. ☺️ Overall, it was a great experience and we’d absolutely stay again. 👌
Top guest favourite
Guest house in Port Perry
5 out of 5 average rating, 88 reviews

Lakeside Guest Suite, on Lake Scugog, Port Perry

LinhRating, 5 stars2 days ago
This place was incredibly clean and comfortable! We were pleasantly surprised to receive a small gift upon arrival—it was such a thoughtful and heartwarming gesture. 🥰 It’s the perfect spot for fishing lovers—you absolutely cannot miss this place if that’s your thing! The location is peaceful and quiet at night, making it an ideal getaway for relaxation.
Guest favourite
Guest house in Innisfil
4.97 out of 5 average rating, 38 reviews

A Greyt Escape

JeffRating, 5 stars2 days ago
Kara's place is great, very clean and very comfortable, the air was great and everything you could ever need for a great stay, beautiful place
Top guest favourite
Guest house in Midland
4.93 out of 5 average rating, 15 reviews

Windfall Cottage On Little Lake

VanessaRating, 5 stars5 days ago
Absolutely love this cottage and the space! Jonathan and Carol are lovely hosts and thought of everything! Any wait to come back
Top guest favourite
Guest house in Barrie
4.98 out of 5 average rating, 82 reviews

Rustic luxury chalet near beach with private pool

DanaRating, 5 stars3 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 Richmond Hill
4.89 out of 5 average rating, 19 reviews

Cozy Guesthouse Heart of RichmondHill Bayview

SalimRating, 5 stars1 month ago
Great place to stay. Host very responsive. We went for a wedding and requested iron and ironing table. Items were delivered by the host through Walmart on the same day. Very clean place and clear instructions provided. I highly recommend the place.
Top guest favourite
Guest house in Uxbridge
4.98 out of 5 average rating, 54 reviews

Private Guest House Retreat

PoojaRating, 5 stars4 days 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!

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 Basement Bedroom with ensuite

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, 27 reviews

Junction Private Laneway Suite with Backyard

MārtiņšRating, 5 stars3 days ago
Nice place, quiet neighbourhood
Guest favourite
Guest house in Markham
4.93 out of 5 average rating, 29 reviews

Chic & Cozy 1Bed Guest Suite

Shehzer KhanRating, 5 stars2 months ago
Had such a beautiful stay at this property! Shayan was incredibly nice and easy to communicate with, which made the whole experience even smoother. The property itself was very clean, well-maintained, and truly equipped with everything I needed. It’s a really lovely space—comfortable, thoughtfully set up, and in great condition. I would absolutely stay here again and highly recommend it to anyone looking for a relaxing and hassle-free stay.
Guest favourite
Guest house in Aurora
4.91 out of 5 average rating, 23 reviews

Delightful One-Bedroom Unit Aurora W/ free Parking

YuRating, 5 stars3 weeks 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.
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!
Guest favourite
Guest house in Richmond Hill
4.89 out of 5 average rating, 37 reviews

Cozy Guest House

GodwinRating, 5 stars1 day ago
Everything about Leila's apartment in the pictures are exactly what is on ground. Extremely clean and decent home ,besides Leila provided everything we needed that made our stay very comfortable. I stayed in this apartment with my wife for 23 days, we didn’t feel like checking out anymore. We had issue with the bed, Leila provided us with a brand new bed within 24 hours . Secondly, our check out time was 11 am, while our departure flight out was 7pm, Leila extended our check out time to 2pm without additional charges. Above all, Leila and her husband, are very humble, kind, friendly and generous people. They received my family warmly and extended same to my children anytime they are around us through out our stay. I will strongly recommend this apartment to families and friends and anyone looking for a decent and world class place to stay in Richmond hill. I will definitely book this apartment again. Thank you Leila, for being kind and nice to my family.
Guest favourite
Guest house in Richmond Hill
4.89 out of 5 average rating, 111 reviews

Entire rental unit Richmond Hill

AminRating, 5 stars2 days ago
Enjoyed my stay with Farzin, would recommend to others. Farzin was very friendly and the place was nice and clean.

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