
Guesthouse holiday rentals in Lake Simcoe
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Top-rated Guesthouses in Lake Simcoe
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Holiday rentals for every style
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Popular amenities for Lake Simcoe guesthouses
Family-Friendly guesthouses

The Boathouse on Sunset Bay Muskoka
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.

friendly house
Very friendly, even helped me find my keys. I will stay there again.

Tiny Cabin in the Forest
Just an amazing weekend. Noreen and Randy were great. Their daughter was also a delight. Just a beautiful area and so peaceful. Can’t say enough about how awesome our stay was. The property and cabin are so beautiful and comfy. The wood stove made for a warm and cozy evening with just the needed amenities to relax and unwind. Fishing little bald lake waters was super productive and visiting in local Bobcaygeon was so much fun. We will definitely revisit this host and their piece of paradise. Can’t say enough about how much fun we had.

Sunny Pines Farm Studio Tennis Court/Bruce Trail
This was my third time there, and as suspected, Vince and Miranda's place never disappoints. Great little space with beautiful views and has all you would need for a weekend away. Will surely return.

haute goat farm | unique alpaca cabin
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]!

1 - Sun Angel Court. Friends and Family Cabin 1
Thank you for making us feel right at home! Really enjoyed our stay.

Private garage apartment near downtown Collingwood
Our second stay at this cozy place. Will definitely be back! Cynthia is a wonderful host!

Family Beach Cottage
We all really enjoyed the cottage! Thank you, Vess, for such a wonderful space.
Guesthouses with a patio

Caledon rural apartment with hot tub and pool
First time staying at this location. It has everything you need to relax in a quiet area that is accessible to everything around the Toronto area but still feel like you are in the country. The pool and hot tub area was great. The hosts answered any questions we had quickly. Even though they lived on the property, we felt like it was a private place. As we have family around the area, we have just found our place to stay for as long as they stay open. I would recommend this place to anyone. Thank you Kathleen and Gerry

The Wilkins - Coach House
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.

Adorable GH in beautiful Claremont/scenic view
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.

The Country Guest House
Beautiful large one bedroom suite in a quiet peaceful location. Very friendly and responsive hosts. The country home feels like home as soon as you enter. Extremely clean and warm atmosphere. Would definitely recommend to anyone needing to come to the area for a quick getaway, a place to spend a weekend or a couple weeks away in the area

Windfall Cottage On Little Lake
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!

Private Guest House Retreat
thank you so much Victoria, I really liked your place. it was very comfortable and cozy. thank you for the treats you left for me, they were delicious! thanks again for being a great host! willl definitely come back!!!

Spacious fully private studio basement & parking
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!

Island Lake Guest House
This my third time staying at Pam & Andrew’s. That should say enough about how much I like their bunkie. Couldn’t ask for a better stay. Everything as described, beautiful setting and only minutes to town.
Guest house rentals with a washing machine and dryer

2 bedroom Guest house in North of Toronto
Samira was very helpful and responsive with all of our concerns. The place was very clean and comfortable, I'd highly recommend it!

"Modern Urban Studio Retreat"
Great stay, easy check-in, unit had extra snacks provided, Shiva was very communicative throughout, would recommend

Fairytale - Spotlessly Clean Getaway - 2 Bedroom
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!

A bright & stylish urban studio
Andrew and Amee were awesome hosts. I arrived just as a blizzard and cold spell began and they were there immediately to clean up the snow and make sure everything was fully operational. Close 5-6 minute walk to the downtown area as well. I enjoyed my home away from home and would love to come back next time I visit Orangeville!

Warnica Coach House
The place was exactly as described. So cute, clean, and felt like home. They clearly put a lot of effort into maintaining the character while adding modern amenities. We had a perfect stay!

Cozy Studio w/ Private Entrance & Parking
Really enjoyed my stay, clean and friendly service. Woyld definitely book here again.

Cozy Studio w/ Private Entrance
Quiet and safe neighbourhood about 35 minutes from city centre with a nice walking path around a pond nearby. Lots of really good restaurants and grocery nearby. Medium sized fenced in yard great for dogs. Clearly marked smoking area. Large driveway spot for car fits SUV. Place was exactly what you expect from the photos - small, but it’s enough space for one person. Host is extremely responsive and helpful. Recommended if you are looking for hassle-free! Tip: there are no bedsheets provided so bring your own double sized. Great stay. Thank you!

Luxury 2 Bedroom 2 Washroom Legal basement Apart
The house is wonderful ,everything very clean of very good taste , I would definitely come back and super recommend !!!
Destinations to explore
- Niagara Falls Holiday rentals
- Grand River Holiday rentals
- St. Catharines Holiday rentals
- Brampton Holiday rentals
- Niagara Falls Holiday rentals
- Niagara-on-the-Lake Holiday rentals
- Muskoka Lakes Holiday rentals
- Vaughan Holiday rentals
- Mississauga Holiday rentals
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- Greater Toronto Area Holiday rentals
- Montreal Holiday rentals
- Ski-in/ski-out rentals Lake Simcoe
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- Blue Mountain Village
- Horseshoe Resort
- Mount St. Louis Moonstone
- Snow Valley Ski Resort
- Port Carling Golf & Country Club
- Gull Lake
- Lakeridge Ski Resort
- Toronto Zoo
- Hockley Valley Resort - Golf, Spa and Ski
- Georgian Bay Islands National Park
- Muskoka Lakes Golf and Country Club
- South Muskoka Curling and Golf Club
- Osler Bluff Ski Club
- Devil's Glen Country Club
- Markham Green Golf Club
- Wolf Run Golf Club
- National Pines Golf Club
- Vespra Hills Golf Club
- Copper Creek Golf Club
- The Paintbrush
- The National Golf Club of Canada
- Jungle Land
- The Nest Golf Club
- LEGOLAND Discovery Centre Toronto