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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 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.
Private room in Markham
4.82 out of 5 average rating, 74 reviews

friendly house

TomRating, 5 stars64 months ago
Very friendly, even helped me find my keys. I will stay there again.
Superhost
Guesthouse 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]!
Superhost
Guesthouse in Wasaga Beach
4.88 out of 5 average rating, 88 reviews

6-Sun Angel Court Cabin 6

JenniferRating, 5 stars10 months ago
Licinia is a wonderful host and went above and beyond to make me feel welcome. The cabin was as described. The deck overlooking the river is relaxing and a great place to chill out. The location is quite close to the Wasaga triathlon so a good spot for participants.
Guest favourite
Guesthouse in Wasaga Beach
4.88 out of 5 average rating, 92 reviews

5- Sun Angel Court (pretty cabin 5)

DiliRating, 5 stars9 months ago
Licinia’s place was amazing. Located super close to the beach, clean, peaceful with a water view and fireplace. She is also very friendly and gave us some recommendations and tips to make the best out of our stay. We will come back!
Guest favourite
Guesthouse 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 ..!!!
Superhost
Guesthouse in Wasaga Beach
4.85 out of 5 average rating, 95 reviews

7-SUN ANGEL COURT, LARGE COUPLES CABIN 7

WendyRating, 5 stars9 months ago
Licinia was the perfect hostess. She was pleasant and friendly, making sure our needs were met. At the same time, she gave us our privacy. We thoroughly enjoyed eating the picnic lunch that we brought, sitting on the dock alongside the Nottawasaga River. - entertained by the geese and the ducks, as well as the various watercraft. The beach was just a short walk across the street in the opposite direction of the river. Although it was too windy to swim, the crashing of the waves was a wonderful sound to hear. The cabin was cute and cozy - all the space that we needed. We enjoyed using the gas bbq on site for dinner - there was even an outdoor cook sink and prep area. Our evening was topped off with a bonfire afterwards. We don’t live far from the Town of Wasaga Beach, but we thoroughly enjoyed our weekend getaway and will most definitely return. We look forward to seeing Licinia and her lovely family again.
Guesthouse 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!

Guesthouses with a patio

Superhost
Guesthouse 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.
Top Guest favourite
Guesthouse in Fergus
5 out of 5 average rating, 21 reviews

Millcreek Riverfront Retreat Elora/Fergus

SarahRating, 5 stars5 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.
Top Guest favourite
Guesthouse in Port Perry
5 out of 5 average rating, 88 reviews

Lakeside Guest Suite, on Lake Scugog, Port Perry

LinhRating, 5 stars1 day 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
Guesthouse in Innisfil
4.97 out of 5 average rating, 38 reviews

A Greyt Escape

JeffRating, 5 stars1 day 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
Guesthouse in Midland
4.93 out of 5 average rating, 14 reviews

Windfall Cottage On Little Lake

ZoraidaRating, 5 stars1 month ago
We were a party of four and had a beautiful, enjoyable long weekend. This is truly a top-of-the-line Airbnb. The care and attention to detail from the hosts made everything effortless and relaxing. From the crisp bedsheets and comfy beds to the magnificent view, everything was perfect. We also appreciated the well-stocked kitchenware, the BBQ, the firepit, and the Adirondack chairs on the deck — every element added to a memorable stay. Would love to return. Thank you for a wonderful experience!
Top Guest favourite
Guesthouse 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!
Top Guest favourite
Guesthouse in Uxbridge
4.98 out of 5 average rating, 54 reviews

Private Guest House Retreat

PoojaRating, 5 stars3 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!
Superhost
Guesthouse in Barrie
4.64 out of 5 average rating, 22 reviews

Cozy Waterfront Boathouse with Lake Simcoe Views

ValeryRating, 5 stars2 weeks ago
Great location near the water, beautiful view. The hosts are very attentive. They solve any issues very quickly.

Guest house rentals with a washing machine and dryer

Guest favourite
Guesthouse 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.
Top Guest favourite
Guesthouse in Grafton
5 out of 5 average rating, 66 reviews

St Anne Spa’s Nearby Secluded Modern Getaway

RebeccaRating, 5 stars1 week ago
We are frequent flyers to Ste Anne Spa but space to stay there is always limited or off site is pricey - this was a great alternative! I myself am an Air BnB host and have now written over 200 reviews, naturally I have a critical eye - this place was great! The space was very clean, great quality, very comfortable and well thought out. Cobourg Walmart was only 15 mins away so we were able to grab some snacks for the night since we arrived later in the day. In addition there was a lovely little patio tucked in too with nice chairs and even a propane fire pit! We will def stay here again.
Guest favourite
Guesthouse in Markham
4.93 out of 5 average rating, 29 reviews

Chic & Cozy 1Bed Guest Suite

Shehzer KhanRating, 5 stars1 month 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
Guesthouse 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.
Top Guest favourite
Guesthouse in Barrie
4.9 out of 5 average rating, 97 reviews

2BR cozy Apt close to dwtn, forests, hospital, hwy

EmiliaRating, 5 stars2 weeks ago
Nicole’s place is vey cozy and fully equipped with all amenities (in good conditions) to hace a great stay. My family and myself really enjoyed this place, not only for the cleanliness, but also the location in north Barrie. We would definitely stay there again in the next trip to Barrie. Highly recommended!
Superhost
Guesthouse 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.
Superhost
Guesthouse in Newmarket
4.71 out of 5 average rating, 21 reviews

Tranquil Spacious Unit

JulieRating, 5 stars2 weeks 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
Guesthouse in Richmond Hill
4.89 out of 5 average rating, 36 reviews

Cozy Guest House

JessicaRating, 5 stars2 months ago
Easy self check-in and had a comfortable stay. Easy access to transit just less than 10 minutes walk to Viva bus on Yonge that goes south to connect to Toronto's TTC. Also close to highway if traveling by car. Host is quick to communicate. Accomodations had everything as described with spacious living area. Would stay again.

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