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Guesthouse vacation rentals in Lake Simcoe

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Popular amenities for Lake Simcoe guesthouse rentals

Family-friendly guest house rentals

Guest favorite
Guesthouse in Bala
4.95 out of 5 average rating, 37 reviews

The Boathouse on Sunset Bay Muskoka

KaraRating, 5 stars7 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 stars61 months ago
Very friendly, even helped me find my keys. I will stay there again.
Guest favorite
Guesthouse in Bobcaygeon
4.97 out of 5 average rating, 206 reviews

Tiny Cabin in the Forest

HojRating, 5 stars4 months ago
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.
Guest favorite
Guesthouse in Orangeville
4.95 out of 5 average rating, 349 reviews

Sunny Pines Farm Studio Tennis Court/Bruce Trail

Yu-HanRating, 5 stars2 months ago
Fantastic property with the back fields. Our dogs had a blast. Some fantastic options for food around. Had an unexpected issue during our stay that is out of their control. They were very responsive and reasonable to communicate with. Will still come back and certainly recommend to others.
Superhost
Guesthouse in Port Hope
4.92 out of 5 average rating, 63 reviews

haute goat farm | unique alpaca cabin

MelissaRating, 5 stars4 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 favorite
Guesthouse in Collingwood
4.89 out of 5 average rating, 171 reviews

Private garage apartment near downtown Collingwood

ErinRating, 5 stars1 week ago
Our second stay at this cozy place. Will definitely be back! Cynthia is a wonderful host!
Guesthouse in Tiny
4.39 out of 5 average rating, 61 reviews

Family Beach Cottage

MarlenaRating, 5 stars18 months ago
We all really enjoyed the cottage! Thank you, Vess, for such a wonderful space.
Superhost
Guesthouse in Wasaga Beach
4.85 out of 5 average rating, 95 reviews

7-SUN ANGEL COURT, LARGE COUPLES CABIN 7

WendyRating, 5 stars6 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.

Guest house rentals with a patio

Guest favorite
Guesthouse in Caledon
4.86 out of 5 average rating, 42 reviews

Caledon rural apartment with hot tub and pool

IanRating, 5 stars6 months ago
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
Superhost
Guesthouse in Cobourg
4.88 out of 5 average rating, 16 reviews

The Wilkins - Coach House

FarrahRating, 5 stars5 months ago
Third stay at the coach house and exceptional as always!
Guest favorite
Guesthouse in CA
4.91 out of 5 average rating, 23 reviews

Adorable GH in beautiful Claremont/scenic view

MalcolmRating, 5 stars11 months ago
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.
Superhost
Guesthouse in Bowmanville
4.75 out of 5 average rating, 4 reviews

The Country Guest House

AndreaRating, 5 stars2 months ago
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
Guest favorite
Guesthouse in Midland
4.92 out of 5 average rating, 12 reviews

Windfall Cottage On Little Lake

AstridRating, 5 stars5 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!
Guest favorite
Guesthouse in Uxbridge
4.98 out of 5 average rating, 47 reviews

Private Guest House Retreat

EnzoRating, 5 stars2 weeks ago
My girlfriend and I had a fantastic stay. Victoria's place is very cozy, clean, welcoming, and beautifully decorated. The highlight for us was the hot tub, surrounded by snow with a clear sky, made our day! She thought about all the details, kitchen and bathroom are also well equipped with all you need Victoria was very understanding and accommodating as well, as our booking fell during the snow storm and we had to adjust a little…everything worked out well in the end 🙏
Guest favorite
Guesthouse in Pickering
4.93 out of 5 average rating, 27 reviews

Spacious fully private studio basement & parking

HariRating, 5 stars2 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 favorite
Guesthouse in Orangeville
5 out of 5 average rating, 44 reviews

Island Lake Guest House

SteveRating, 5 stars1 month ago
Pam and Andrew were great hosts. I spent two weeks there and they were very responsive if I had any questions or needed anything. Place was very clean, just like the pictures. Location is great, close to everything in a quiet neighbourhood. Also a super friendly dog that comes to greet you from time to time!

Guest house rentals with a washer and dryer

Superhost
Guesthouse in Newmarket
5 out of 5 average rating, 4 reviews

New Spacious Airy Guest-home

OmidRating, 5 stars3 months ago
The place was clean and comfortable. Sima was very cooperative and caring. I recommend this place to anyone who is looking for a nice stay in GTA.
Guest favorite
Guesthouse in Markham
4.89 out of 5 average rating, 38 reviews

2 bedroom Guest house in North of Toronto

RichardRating, 5 stars3 weeks ago
another great stay. this is the first one I seatch for when needing to book in Markham.
Guest favorite
Guesthouse in Richmond Hill
4.98 out of 5 average rating, 59 reviews

"Modern Urban Studio Retreat"

Maria SophiaRating, 5 stars1 week ago
Wonderful stay with Shiva! The place has everything you need for a short or long stay. When we arrived, it was clean and the host left a thoughtful welcome card with our names and some treats. Thank you!
Guest favorite
Guesthouse in Newmarket
5 out of 5 average rating, 72 reviews

Fairytale - Spotlessly Clean Getaway - 2 Bedroom

AliciaRating, 5 stars1 month 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!
Guest favorite
Guesthouse in Orangeville
4.96 out of 5 average rating, 126 reviews

A bright & stylish urban studio

JonathanRating, 5 stars1 month ago
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!
Guest favorite
Guesthouse in Barrie
4.99 out of 5 average rating, 143 reviews

Warnica Coach House

RavenRating, 5 stars1 day ago
The most thoughtful, and comfortable stay I have ever had in a BnB. It really felt like they had gone through and thought of absolutely everything. It was so beautiful! There’s a lovely little book inside that tells your the Warrica family as well.
Guest favorite
Guesthouse in Richmond Hill
5 out of 5 average rating, 5 reviews

Cozy Studio w/ Private Entrance & Parking

VictoriaRating, 5 stars1 month ago
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!
Superhost
Guesthouse in Ajax
4.63 out of 5 average rating, 24 reviews

Luxury 2 Bedroom 2 Washroom Legal basement Apart

RenataRating, 5 stars2 months ago
The house is wonderful ,everything very clean of very good taste , I would definitely come back and super recommend !!!

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