Holiday houses in Simcoe Island

5 out of 5 average rating, 183 reviews

Houseboat in Yarker

4 season cabin in the woods -A romantic Riverboat!

You won’t forget this memorable experience! A 1974 River Boat has been lovingly transformed in to a whimsical all season cabin. Come for the fantasy then bask in the comfort and romance of it. Luxurious amenities include everything but the kitchen sink..literally! A perk to no running water is that I do your dishes at my place while you relax! The houseboat is tucked in to the trees and just across the road from a lakefront park. Plus...a Playshed full of seasonal outdoor equipment is included!

4.97 out of 5 average rating, 164 reviews

Loft in Greater Napanee

Luxurious Victorian Loft on the Doorstep of PEC

A fully private luxury loft apartment located in historic downtown Napanee and on the doorstep of Prince Edward County, offering everything you have been looking for and more. From the moment you arrive you will be taken by the beauty of this regal Victorian property. This space has been designed with your comfort in mind. You will also enjoy a beautiful outdoor space perfect for relaxing or dining, and lined with stunning gardens. Perfect for your romantic getaway, wine tour, or city escape.

Guesthouse in Township Of Frontenac Islands

4.97 out of 5 average rating, 109 reviews

Wolfe Island Oasis

Welcome to our cozy country retreat. Our guesthouse offers everything you need to unplug from the hustle of the city. Whether its enjoying a coffee on the lounge chair while watching the sunrise; stargazing on the patio; sitting around a warm campfire; or falling asleep under our son's handcrafted cedar strip canoe: this retreat was designed to maximize a unique experience. The building is completely separate from our family hobby-farm and offers a secluded space for our guests.

4.99 out of 5 average rating, 438 reviews

Capitan Burn's House on Wellington

Superb location in historic downtown Kingston, 3 blocks from princess street, walking distance to Queens, waterfront, City park, both hospitals, and the K-Rock center. Short drive to RMC and Fort Henry. Fully outfitted kitchen and beautiful courtyard. Fully renovated 175 year old Historic limestone building, with a cozy gas fireplace for the winter. If you need more space or the dates booked, please check out our other listing! airbnb.com/h/kingstonloft Licence #: LCRL20210000899

4.91 out of 5 average rating, 144 reviews

Apartment in Kingston

The Sweet Suite

- This bright, peaceful and quiet private apartment has an abundance of amenities at your home away from home. Enjoy this space and explore what Kingston has to offer from its convenient central location. - Separate exterior entrance. - Sound treated ceilings and walls. - Beautiful wooded area, park, and walking paths behind the property. - Two tobogganing hills within walking distance. -Complimentary snacks. -Linens washed after each stay with o3 commercial grade laundry system

4.96 out of 5 average rating, 174 reviews

Treehouse in Tweed

Off-Grid Tree Canopy Retreat

Escape to this private off-grid retreat, nestled high in the trees overlooking the natural beauty of the Moira River. This elevated nature shelter provides a cozy, rustic space for guests seeking solitude, adventure, or a peaceful getaway. This is a multi-use nature retreat designed to provide shelter and relaxation in a secluded setting. Guests are welcome to rest and recharge in the space, enjoying the warmth of the wood stove while taking in the peaceful surroundings.

5 out of 5 average rating, 334 reviews

Cabin in Marlbank

The Woodland Escape

Step back in time. Experience living in a one room cabin heated by a wood stove and lit by candles and lanterns. Your bathroom is an outhouse. There is no running water or electricity. You can ski, snowshoe or hike on the 40 acre property. Also, within minutes of the cabin are numerous trail systems, lakes and beaches. If you want to go further back in time, you can visit our 1700’s settler’s cabin. Check out our YouTube channel, “The Woodland Escape”

4.94 out of 5 average rating, 232 reviews

Cozy home 2 + bedrooms in Kingston Ontario

Updated and freshly painted 2 bedroom home. Fully furnished and equipped. Spacious and bright, this home is perfect for business or pleasure. Sleeping for 5, laundry, parking, all conveniences. BBQ and back yard seating area. Brand new mattresses. Located in a quiet neighborhood and close to everything. Grocery store. Tim Horton's, Gas station, Walmart, fast food and restaurants within 5 minutes. Kingston STR License # LCRL20220000367

4.94 out of 5 average rating, 132 reviews

Victorian Boutique Apartment-Steps from Lakeshore!

Enjoy the elegance of a by-gone era while staying in this stunning Victorian loft, located on a quiet leafy boulevard in the heart of Kingston’s most historic and architecturally eclectic neighborhood! Beautifully decorated and featuring a bright vaulted grand living room with a tin clad mezzanine supported on original exposed beam, exposed brick, period furniture, and a stunningly unique black-and-white tiled bathroom.

4.97 out of 5 average rating, 102 reviews

Guest suite in Kingston

Hotel Room Bela in downtown Kingston

A small and cozy hotel room accommodation with a private entrance to your own space and free parking until check out, located in downtown Kingston's Sydenham Ward. You are steps away from the heart of downtown shopping, restaurants, Hotel Dieu Hospital and 3 blocks from Queen's University and KGH. Our space is small at 175 sq ft, but you’ll have everything you need for a comfortable stay. Licence: LCRL20230000508

4.86 out of 5 average rating, 287 reviews

Beautiful new church basement

Non-Smokers Only If booking please provide information about your group and what brings you to Kingston. Entire private church basement in beautiful historic Portsmouth Village in Kingston. This stunning all newly renovated 170 year old limestone church is perfect for a get away weekend or if you are coming for a Kingston Penitentiary Tour. Licence number LCRL20220000037

4.92 out of 5 average rating, 298 reviews

Tiny home in Perth

Off-grid A-frame cabin

Welcome to “The Hemlock” cabin A unique stay situated minutes from historic Perth, Ontario. The Hemlock sits on 160+ acres of private, natural forest. Enjoy 3 season lake access for kayaking & canoe. Year round trails for hiking, snow shoeing, exploring etc. Beautiful scenery in a peaceful, private setting, relax and unwind by the fire! We look forward to having you! (:

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Other great holiday rentals in Simcoe Island

4.94 out of 5 average rating, 34 reviews

Dome in Greater Napanee

glamping farm bubble

MirandaRating, 5 stars2 weeks ago

This was such an unforgettable stay!!!! James was fantastic, friendly and went over the top for us. We will definitely be back. The communication was better than we could have ask for. Every personal touch didn’t go unnoticed! Thank you again!

4.86 out of 5 average rating, 7 reviews

Cottage in Wolfe Island

Sandra's Wee House on Simcoe Island

FranckRating, 5 stars7 months ago

This place is nothing short of breathtaking. The cottage itself is warm and cosy and you know it is used by its owners which adds tons of authenticity. The island is perfect when you have young kids... they can basically go anywhere they want, run, shout.... The landscape is like a dream, we've been gifted with one of the best sunset one can dream of. A truly authentic Canadian cottage... and if you need something, you can just hop on the short ferry and get it at the Wolfe Island dépanneur. And finally, the hosts... excellent, responsive and made us feel like friends using their cottage. We needed a peaceful place to chill and have our kids enjoying themselves, we found it. 6 star, will definitely come back. Merci Sandra and Rebecca.

5 out of 5 average rating, 26 reviews

Guesthouse in Kingston

Tiny Home Retreat with Fire Pit and Hot Tub!

AshleyRating, 5 stars1 week ago

Sure! Here’s a polished Airbnb review you can use or adapt: ⭐️⭐️⭐️⭐️⭐️ 5/5 Bryan’s place was exactly what we were looking for — very private, super clean, and incredibly relaxing. The hot tub and firepit were awesome — well maintained and perfect for unwinding in the evening. Everything was spotless and thoughtfully set up, and the location was great for getting around but still felt like a quiet retreat. Would absolutely stay here again!

Cottage in Frontenac Islands

5 out of 5 average rating, 6 reviews

Waterfront home, beautiful Simcoe Island getaway

AshleyRating, 5 stars9 months ago

Sabrina's place was extremely quaint and a great experience. What a cool experience being on such a remote area. The second, small ferry operators were very friendly and a pleasure to see. Sabrina's property was extremely well taken care of and has everything you need. The views were incredible and beautiful. I would definitely recommend this place 😊

4.93 out of 5 average rating, 45 reviews

Tiny home in Thomasburg

Loft in the Wild Glamping Cabin in the Woods

CrystalRating, 5 stars2 weeks ago

This was our first time glamping, and it couldn't have been more perfect. My husband wanted the outdoorsy camping feel, and I was looking for something more aesthetic and luxurious—this place gave us the best of both worlds. The space was quiet, cozy, and beautifully set up. It felt like our own little hideaway, peaceful and private, yet thoughtfully prepared with every detail in mind. The hosts communicated everything clearly and respectfully, which made us feel both welcomed and left alone to enjoy the experience. It was truly a magical night away—exactly what we needed. Highly recommend for couples looking to unplug and reconnect.

4.92 out of 5 average rating, 26 reviews

Home in Bath

Lakefront with Sauna & Trails

ShubhroRating, 5 starstoday

We had a wonderful stay at this beautiful waterfront property! The home was spotless, well-equipped, and incredibly comfortable. Check-in was a breeze with clear instructions, and the location is perfect—just a short drive to Kingston, but still peaceful and relaxing by the water. The views were stunning, and the outdoor space was perfect for unwinding. The host was very responsive and helpful, making the whole experience smooth from start to finish. Highly recommend and would definitely stay again!

4.89 out of 5 average rating, 46 reviews

Guest suite in Kingston

Tree top views and exposed beams.

DennisRating, 5 stars6 days ago

My partner and I stayed here for a weekend and it's a 15 minute drive to Kingston. it was very well equipped and spacious for two people, with beautiful morning sunrays coming through the windows and greenery everywhere. Lisa was a great host for answering all of our questions promptly and we felt very at home at their guest suite. We would come back again next time!