Holiday rentals in Simcoe Island

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Top-rated holiday rentals in Simcoe Island

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Top guest favourite
An A-frame house is presented with a blue exterior amidst a snowy landscape. The structure showcases a sloped roof with multiple windows and a door leading to a deck. Surrounding trees, partially covered in snow, create a serene and natural setting.
Home in HUNT
4.98 out of 5 average rating, 222 reviews

Modern & Charming Eh-Frame | 4-Season Chalet

Escape the everyday chaos and unwind in this romantic A-frame home. Nestled on 36 acres of forest and marshland, this charming getaway will fulfill any couple’s desire for a private weekend in the woods to indulge in a deep connection with each other and with nature. High loft ceilings, exposed beams, wood burning fireplace, a cozy loft bedroom, spacious shower for two, and sunken soaker bathtub create an intimate and pleasing ambiance for your carefree retreat. Hosts an abundance of wildlife.

Guest favourite
Yurt in Madoc
4.93 out of 5 average rating, 638 reviews

Forest Yurt

Yurt in a private forest area. Walking distance to the cheese factory (ice cream, lunches, snacks), produce stands, and a park. Short drive to Madoc (groceries, beer/ LCBO, parks, beach, bakery, restaurants, etc). Perfect area for star gazing, long walks & bike rides. This yurt is in a camping setting, with indoor compost toilet, seasonal private outdoor shower, no wifi but there is electricity, dishes, indoor hot plate, BBQ, mini fridge, all pots & pans and bedding and clean drinking water.

Guest favourite
The cabin is situated on a gently sloping green lawn surrounded by trees. A spacious deck is visible, complemented by outdoor furniture. A landscaped area with stone walls and plants can be seen in the foreground, enhancing the natural setting.
Cottage in Leeds and the Thousand Islands
4.92 out of 5 average rating, 231 reviews

Smugglers Getaway on the St. Lawrence River

Enjoy your privacy in this waterfront cabin in the historic Smugglers Cove on the St. Lawrence River in the heart of the 1000 Islands. You'll have use of the entire cabin with fantastic River views from your own patio. Conveniently located off of the 1000 Islands Parkway, one of the most beautiful scenic drives in North America, guests may enjoy walking, hiking and cycling the paved and scenic 37 km Waterfront Trail. You're welcome to arrive by boat or car; private entrance to your cabin.

Top guest favourite
A charming guesthouse is set in a vibrant garden, featuring a spacious deck overlooking the landscape. Lush greenery and flowers surround the building, enhancing the natural environment. A tree provides shade, and clear blue skies add to the serene atmosphere.
Guest house in Township Of Frontenac Islands
4.98 out of 5 average rating, 146 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.

Top guest favourite
An evening view of the cabin's entrance is lit by soft outdoor lighting. A welcoming porch features a wooden railing and decorative elements, while plants surround the steps. The structure has large glass windows, allowing a glimpse of the interior ambiance.
Farm stay in Newburgh
5 out of 5 average rating, 118 reviews

Escape Goat Hideaway at Barking Goat Farms

“Glamping” at its best. Come experience an off grid all season cabin, tucked away in a very private location at Barking Goat Farms, between Toronto and Ottawa. Enjoy your morning coffee on the lovely screened in porch and spend you evenings around the campfire star gazing amid the peaceful surroundings. Many local attractions to visit or just unplug and relax. Perfect for a couples romantic escape or a fun girls getaway. Enjoy a complimentary meet and greet with our goats and donkeys

Guest favourite
Dome in Plainfield
4.8 out of 5 average rating, 178 reviews

From quiet rivers to starlit skies,

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!

Top guest favourite
A cozy living area features a rustic wood stove, complemented by two stylish chairs and a vibrant area rug. Large windows frame the serene view of Lake Ontario, enhancing the space's inviting ambiance.
Guest house in Prince Edward
4.98 out of 5 average rating, 274 reviews

Little Ben Prince Edward County

Little Ben's license allows 2 adults and one child age 10 and under. Located 10 feet from Lake Ontario, in the heart of beautiful Wellington, Little Ben is a fully renovated 1 bedroom cottage in the centre of wine country. Little Ben offers a fully equipped kitchen, a dining area and a comfy living area with a wood stove. The true glory of Little Ben exists outside its walls--you are just a mere ten steps down to your own limestone beach on Lake Ontario! Licence # ST-2019-0358

Superhost
A white geodome is situated on a raised wooden deck, surrounded by lush green grass and trees near the water's edge. The calm surface of Varty Lake reflects the vibrant blue sky and the natural scenery.
Dome in Yarker
4.93 out of 5 average rating, 131 reviews

Sky Geo Dome on the Lake

Our beautiful geodome offers a unique glamping experience with breathtaking lake views. Perfect for romantic getaways, celebrations or family vacations. Enjoy stunning sunrises, stargaze, roast marshmallows by firepit, BBQ, play air hockey/pool/axe throwing, enjoy a night sky projector -indulge in peace & serenity. Varty Lake is ideal for fishing, kayaking & canoeing. Just 15 min from amenities & 30 min from alpaca farms, wineries, 1000 Islands, & stargazing in Stone Mills.

Top guest favourite
A comfortable living area features two brown armchairs and a spacious light-colored sectional. A mounted flat-screen television remains positioned above a wooden media console. A round mirror is displayed above a fireplace, contributing to the cozy ambiance of the space.
Home in Kingston
5 out of 5 average rating, 194 reviews

The Urban Cottage on Earl

The Urban Cottage on Earl is located in the heart of Kingston's historic Sydenham Ward and is within 2-3 blocks of KGH, Hotel Dieu, Queen's University, Lake Ontario and Kingston's vibrant downtown. Whether you are coming to Kingston for work or play, The Urban Cottage has all the conveniences of a downtown city home coupled with a relaxed cottage feel. After a long day, enjoy the fully enclosed, private backyard oasis complete with hot tub and water feature. LCRL20230000005

Top guest favourite
An open living area features a modern kitchen island with bar stools, complemented by a comfortable seating nook. Natural light floods the space through large windows, revealing a peaceful winter landscape. The rustic coffee table and simple decor enhance the cabin's cozy ambiance.
Cabin in South Frontenac
5 out of 5 average rating, 98 reviews

Our Lakeside Getaway

Enjoy the beauty of South Frontenac from the quiet comfort + modern luxury of our lakeside cabin. Located in Eastern Ontario’s cottage country, our cabin is nestled on a small, peaceful lake 15 minutes west of Westport, Ontario. This space is ideal for 1-2 adults. This newly renovated cabin sits on a shared 3-acre property with our family’s lake house. This home-away-from-home has been in our family for 17 years + we’re thrilled to share a piece of our paradise with you.

Top guest favourite
A treehouse sits elevated beside a gently flowing river, surrounded by lush greenery. Stairs lead to the entrance, while the water's smooth surface reflects the vibrant hues of the trees above, creating a serene atmosphere within nature.
Treehouse in Tweed
4.95 out of 5 average rating, 251 reviews

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

Top guest favourite
The bedroom features a queen size bed with a tufted headboard, complemented by two bedside tables, each with a decorative lamp. A soft, neutral blanket covers the foot of the bed, and subtle artwork adorns the wall above the headboard.
Flat in Kingston
4.98 out of 5 average rating, 165 reviews

Spacious Downtown Loft

This spacious downtown 2 level loft is the perfect location to enjoy everything that Kingston has to offer. Walking distance to the Grand theatre, Slush Puppie Place, restaurants, universities, ferry, and Fort Henry. The perfect location for an evening or weekend getaway to explore Kingston, visit family or just unwind and relax. No parking available with the property (see more detail under Location - Getting Around) City of Kingston License #LCRL20220000211

Popular amenities for Simcoe Island holiday rentals

  1. Airbnb
  2. Canada
  3. Ontario
  4. Frontenac County
  5. Frontenac Islands
  6. Simcoe Island