Holiday rentals in Simcoe Island

5 out of 5 average rating, 184 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!

4.98 out of 5 average rating, 108 reviews

The Cottage on Vine - Near Historic Downtown

Welcome to the Cottage on Vine! Nestled in a charming urban setting, your downtown retreat is just a short stroll from vibrant Princess Street and Queen’s University. Featuring two comfortable bedrooms and a bright, well-equipped bathroom, enjoy the comforts of home with complimentary self-serve tea and coffee. When you stay at the Cottage, you'll also enjoy free parking, an on-site washer/dryer, high-speed Wi-Fi, and a smart TV with Netflix. Experience a unique blend of comfort and convenience!

Guest house 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.

Superhost

Dome in Plainfield

4.83 out of 5 average rating, 120 reviews

The Bubble Glamp Inn.

Experiencing forest bathing while you are also enjoying the comfort of our bubble, Escape the hustle of the modern lifestyle and re-balance your Self with the rythme of nature. Inside, there is a Queen-size bed and wood stove will keep you toasted. No running water; you will find an outhouse a few steps away from the dome. Cook outside on the BBQ, relax in the hamac and explore nature on our trail or in a kayaks or paddle board. A unique way to enhance your experience? Rent a sauna!

4.91 out of 5 average rating, 147 reviews

Flat 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, 176 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, 335 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, 133 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.

4.96 out of 5 average rating, 347 reviews

Flat in Kingston

Historic Apartment Downtown Kingston

Recently renovated, space includes a fully equipped kitchen and a luxurious bathroom with heated floors. Superb location in historic downtown kingston. Three blocks from Princess St, walking distance to queens, the waterfront, city park, both hospitals and the Leon's center. Short drive to RMC and Fort Henry. Includes a private outdoor space with seating and a BBQ Licence #: LCRL20220000146

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! (:

4.95 out of 5 average rating, 150 reviews

Tiny home in Newburgh

Just Around the Corner Cabin

***No Cleaning Fee*** This glamping experience is tucked away in the village of Newburgh. The bunkie is 30 minutes from downtown Kingston and 15 minutes from Napanee and 40 minutes from Picton. It is conveniently across the road from the Cataraqui Trail. The well-maintained, beautiful trail is ideal for nature-enthusiasts who enjoy hiking, cycling or jogging.

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Other great holiday rentals in Simcoe Island

5 out of 5 average rating, 83 reviews

Guest suite in Kingston

Newly renovated downtown suite!

CorrieRating, 5 stars2 days ago

We loved this place for our family of four! They made us feel at home. The space is lovely and cozy. Wish we could have stayed longer!

Yurt in Leeds and the Thousand Islands

5 out of 5 average rating, 66 reviews

Luxury Eco-Yurt | Nature Escape by Charleston Lake

GurpreetRating, 5 stars2 weeks ago

Stayed in an amazing yurt last night — cozy, clean, and super peaceful. A perfect escape into nature. Highly recommend!

Superhost

Cabin in Frontenac Islands

4.6 out of 5 average rating, 15 reviews

Windy Island Homestead Cabin

EmilyRating, 5 stars9 months ago

I can’t say enough about Virginia and her amazing retreat. We were looking for a simple halfway stop on our way home from seeing family in the US and found this amazing space run by wonderful people. It was a treasure and we will be back. This beautiful family is forging a new way of living and travel that is sustainable and gives me hope. She is a great host if you have children and are interested in forest school and learning about local history and geography. My son was free to run and hear nothing but nature sounds and then we took the ferry everyday into Kingston to explore Canadian history and culture and eat amazing food. We went to the Wolfe Island hotel to eat local wonderful food and visited the stunning isolated beach every night at sunset. Wolfe Island is a place like no other. I had such a great connection with the host and her commitment to the earth and the future. Thank you Virginia!

4.96 out of 5 average rating, 97 reviews

Guest house in Perth

Stay on the Tay! A Charming Stone Guest House

DavidRating, 5 stars3 weeks ago

Kate's place is quite lovely and provides an opportunity to be a part of Glen Tay Valley history. The Garden's are beautiful and sitting in the summer house is a treat. Great place for reading a book with a glass of wine in hand. Our dog loves it there too as he can watch the bird life by the Tay river. Kate's digs are a great spot for resting in between adventures in the Perth area. Absolutely charming. It was our third time back.

4.54 out of 5 average rating, 112 reviews

Entire Private Suite

Peter Rating, 5 stars2 weeks ago

Great place for the money. There wasn’t a full kitchen but a huge fridge and a microwave. On site parking. It’s only a 9 minute drive to the main hub of Kingston, where lots of cool shops and restaurants abound. Bathroom was nice and clean, comfortable bed and huge TV with most streaming services easily accessible. Very quiet neighborhood at night.

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.

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 😊