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Guesthouse holiday rentals in Lake Simcoe

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Popular amenities for Lake Simcoe guesthouses

Family-Friendly guesthouses

Guest favourite

Private room in Ajax

4.92 out of 5 average rating, 12 reviews

CB1 - spacious Rm with prvt washroom -no parking

MarkRating, 5 stars12 months ago
I had a great connection with Syed. I could tell he has been a host for some time as his rooms were booked right away so he knows what he's doing. I also believe it's because of Syed's friendly manner and prompt response to questions. The room and amenities were exactly what I needed and I already stayed twice. His Airbnb is at the top of the list when I stay in Ajax and I would recommend his listing to anyone. Great job Syed.
Guest favourite

Guesthouse in Bala

4.95 out of 5 average rating, 37 reviews

The Boathouse on Sunset Bay Muskoka

KaraRating, 5 stars6 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 stars60 months ago
Very friendly, even helped me find my keys. I will stay there again.
Guest favourite

Guesthouse in Bobcaygeon

4.97 out of 5 average rating, 206 reviews

Tiny Cabin in the Forest

HojRating, 5 stars3 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 favourite

Guesthouse in Orangeville

4.95 out of 5 average rating, 348 reviews

Sunny Pines Farm Studio Tennis Court/Bruce Trail

KaylaRating, 5 stars2 months ago
We enjoyed a nice mini vacation at Sunny Pines. We spent some time at the Scandinave spa and did some shopping in Collingwood which was about a 45 minute drive away. The property is beautiful and access to the sauna was a nice bonus. Everything we needed was there and the loft was very clean with fresh towels and linens. The only criticism would be that the instructions to the building weren’t clear (it’s the loft on top of the garage). We would definitely recommend this Airbnb to those looking for a relaxing weekend away.
Superhost

Guesthouse in Port Hope

4.92 out of 5 average rating, 63 reviews

haute goat farm | unique alpaca cabin

MelissaRating, 5 stars3 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

Guesthouse in Collingwood

4.89 out of 5 average rating, 170 reviews

Private garage apartment near downtown Collingwood

KevinRating, 5 stars5 months ago
Great place to stay, worth the money, it was close to downtown and the hosts were very friendly!

Guesthouse in Tiny

4.39 out of 5 average rating, 61 reviews

Family Beach Cottage

MarlenaRating, 5 stars17 months ago
We all really enjoyed the cottage! Thank you, Vess, for such a wonderful space.

Guesthouses with a patio

Guest favourite

Guesthouse in Caledon

4.86 out of 5 average rating, 42 reviews

Caledon rural apartment with hot tub and pool

IanRating, 5 stars5 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 stars4 months ago
Third stay at the coach house and exceptional as always!
Guest favourite

Guesthouse in CA

4.91 out of 5 average rating, 23 reviews

Adorable GH in beautiful Claremont/scenic view

MalcolmRating, 5 stars10 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.
Guest favourite

Guesthouse in Fergus

5 out of 5 average rating, 18 reviews

Millcreek Riverfront Retreat Elora/Fergus

KelseyRating, 5 stars1 month ago
We had a lovely stay at Amy’s guesthouse. Everything was perfect and the place was so clean and cozy. We would love to come back in the summer for another relaxing getaway.
Superhost

Guesthouse in Bowmanville

4.75 out of 5 average rating, 4 reviews

The Country Guest House

AndreaRating, 5 stars1 month 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 favourite

Guesthouse in Uxbridge

4.98 out of 5 average rating, 46 reviews

Private Guest House Retreat

polinaRating, 5 stars3 weeks ago
We were looking for a couple’s getaway in the area, as we booked a day in a spa in Markham. This AirBNB is super cozy, tidy, warm and welcoming. Victoria was super responsive and friendly. We had some fresh pastries waiting for us - such a lovely and sweet welcome. The place is private but on a side road, not within walking distance of anything, but 100% as expected. We would definitely come back if we were looking into staying in this area.
Guest favourite

Guesthouse in Pickering

4.93 out of 5 average rating, 27 reviews

Spacious fully private studio basement & parking

HariRating, 5 stars1 month 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 favourite

Guesthouse in Orangeville

5 out of 5 average rating, 42 reviews

Island Lake Guest House

BenRating, 5 stars1 month ago
A cozy spot for a little getaway. The fireplace creates a very soothing atmosphere and the bed is very comfortable. Quite spacious for the size. The large shower was also a plus.

Guest house rentals with a washing machine and dryer

Guest favourite

Guesthouse in Markham

4.88 out of 5 average rating, 34 reviews

2 bedroom Guest house in North of Toronto

RichardRating, 5 stars2 weeks ago
Great walk out basement, made it feel roomy and didn't feel like we were staying in a basement. met all our needs.
Guest favourite

Guesthouse in Richmond Hill

5 out of 5 average rating, 49 reviews

"Modern Urban Studio Retreat"

KyleRating, 5 stars1 week ago
Wonderful stay here. Spotlessly clean, cozy and quiet. Very convenient location and in a nice neighbourhood.
Guest favourite

Guesthouse in Newmarket

5 out of 5 average rating, 71 reviews

Fairytale - Spotlessly Clean Getaway - 2 Bedroom

AliciaRating, 5 stars3 weeks 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 favourite

Guesthouse in Toronto

5 out of 5 average rating, 59 reviews

Designer Beach Retreat.

MelissaRating, 5 stars2 months ago
This is a lovely alternative to staying in downtown Toronto. Ashley was a wonderful host. The cottage is modern, well equipped, super cozy and spotless. We loved the Sonos throughout the house and enjoyed the beautiful kitchen and living room space. It is about a 25-30min commute to downtown Toronto but easy public transport and onsite parking. Beautiful beach walk nearby at Kew and Woodbine beaches. Thanks for a nice visit! Highly recommend and wish we had more time to explore the cool neighborhood
Guest favourite

Guesthouse in Barrie

4.99 out of 5 average rating, 131 reviews

Warnica Coach House

ElijahRating, 5 stars1 week ago
Felt right at home right away! Such a lovely little space, beautiful aesthetic, and supplied with everything you need for a night away! Couldn’t be happier with our stay, thank you so much!
Superhost

Guesthouse in Richmond Hill

5 out of 5 average rating, 4 reviews

Cozy Bachelor Suite w/ Private Entrance & Parking

AnnaRating, 5 stars1 month ago
My dad stayed here for about a week, and overall, he really enjoyed his time. The place was clean, comfortable, and well-maintained. Everything was as described in the listing, and the host was responsive and helpful. It was a pleasant experience, and we would recommend this place to others. 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 stars4 weeks ago
The house is wonderful ,everything very clean of very good taste , I would definitely come back and super recommend !!!
Guest favourite

Guesthouse in Port Perry

4.97 out of 5 average rating, 66 reviews

Port Perry Island Krazee Acres Hobby Farm

BryanRating, 5 stars1 month ago
This was our second time at Debbie and Rob’s place and we enjoyed it very much. It is a great escape if you want to rest, watch movies, cook and relax during the winter months. We stayed cozy the entire time. Debbie is an amazing communicator and a warm and welcoming host. We recommend it!

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