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, 215 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.

Top guest favourite
A spacious deck offers comfortable seating with two armchairs and a sofa, all featuring red cushions. A coffee table sits in the center, providing a place to relax while enjoying views of the calm lake and surrounding greenery.
Cottage in Sydenham
4.94 out of 5 average rating, 192 reviews

Luxury on the Lake

Reconnect with nature at this unforgettable cottage escape. Perfect for families, couples, or anyone wanting to relax! Furnished with clean modern furniture. Beautiful, refreshing Sydenham Lake is steps from the cottage and the water is very deep off the dock so jump right in!! or fish, paddleboard, snorkel, paddle boat, canoe, whatever calls to you! Cottage is a 20 min walk to the town of Sydenham (which has a sandy public beach, boat launch, LCBO, Foodland, etc.) and 20 min drive to Kingston.

Top guest favourite
A master bedroom features a queen-size bed with a textured white coverlet. Large windows and sliding glass doors allow for natural light and offer views of the waterfront. A small table is positioned near the window for additional functionality.
Cottage in Hammond
4.97 out of 5 average rating, 175 reviews

River Ledge Hideaway

New construction home designed specifically with the thought of guests in mind overlooking the Saint Lawrence River. Enjoy a memorable fall or holiday getaway to this waterfront oasis. Highlighting this home is a large master bedroom overlooking numerous islands speckled throughout the expansive water view. Outdoor fire pit and grilling area will be set up for the fall season. Walk down our path to your own private waterfront. Great place for couples, small families or friends getting together

Guest favourite
An A-frame cottage is framed by lush greenery, featuring a dark wood exterior with a centrally located white door. An overhanging carport provides coverage for vehicles, while hanging planters add a touch of color to the entrance. A pathway leads to the cozy front yard.
Cottage in Sandy Creek
4.96 out of 5 average rating, 336 reviews

🌙 Olde Salem A-Frame Cottage 🔮 near Lake Ontario

You are steps away from witnessing the greatest sunsets along North Sandy Pond (across from Lake Ontario) when you stay at our relaxing, unique, and cozy A-frame - inspired by all things magical and earthy. Sit by the backyard fire, sip coffee by the electric fireplace, read a book in the bedroom nook, play board games, dance in the kitchen, and enjoy four seasons of nearby activities such as fishing, kayaking, boating, jet skiing, hiking, swimming, ice fishing, snowmobiling, and snowshoeing.

Superhost
A modern kitchen is displayed, featuring stainless steel appliances and a stylish backsplash. High ceilings are complemented by exposed beams, while windows with soft curtains allow natural light to filter in. The open layout creates a seamless connection to the adjoining living space.
Flat in Kingston
4.79 out of 5 average rating, 841 reviews

Waterfront suite over looking Lake Ontario

Additional upgrades such as large granite counter tops, brand new furniture, stainless steel appliances, high ceiling. Fine finishes show the care that have gone into the history of this limestone suite located in one of the best locations in the heart of downtown Kingston. Please note: Our place does not have an elevator and is located on the third floor. Guests will need to climb two flights of stairs to access the unit. This may be challenging for seniors or guests with limited mobility.

Guest favourite
Dome in Plainfield
4.8 out of 5 average rating, 173 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!

Guest favourite
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, 128 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 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, 252 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 exterior of a historic brick house features decorative architecture with arched windows and a front porch adorned with intricate details. Leafless trees frame the entrance, while a manicured shrub is visible beside the steps leading to the welcoming front door.
Guest suite in Kingston
5 out of 5 average rating, 120 reviews

Historic Bela in downtown Kingston

Welcome to Historic Bela, in the heart of downtown Kingston. Built in 1889 and completely renovated with one bedroom and a den, our house still shows its historic charm with the original front doors, exposed brick, fireplace (non-functional) and stained glass. Our prime location with free parking for one vehicle until check out, allows you to walk to an array of restaurants, shop at unique local stores, Queen's University and our 2 hospitals. Licence: LCRL2023000050

Top guest favourite
Guest suite in Kingston
4.97 out of 5 average rating, 306 reviews

Bright + Cozy Fireplace Basement Suite w/ Parking

Welcome to our bright, cozy, and licensed basement apartment in Kingston's west end. Enjoy fresh, locally-roasted, coffee each morning and spend the evening beside the gas fireplace. With parking for one vehicle, you'll find yourself under 10 minutes away from the mall, local restaurants, and the Invista Centre—and a quick 18-minute drive to downtown. Whether you're here with a purpose or just looking to wander, we've got you covered. License #: LCRL20210000493

Top guest favourite
Flat in Kingston
4.98 out of 5 average rating, 160 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

Top guest favourite
A single-story home is situated on a quiet street, surrounded by lush green landscaping. The house features a gray exterior with white trim, a welcoming front porch with steps, and large windows inviting natural light into the interior.
Home in Kingston
4.99 out of 5 average rating, 153 reviews

Central Kingston Urban Oasis

Enjoy a cozy home central to the downtown core of Kingston, available May to September. On a quiet street, you will be less than a 5 minute drive to Queen’s University, hospitals, and many attractions that Kingston offers. You will appreciate this peaceful setting that is so accessible to the main arteries. High speed Bell fibe internet available and Netflix. We are a short term rental licensed with the city of Kingston #LCRL20220000554.

Popular amenities for Simcoe Island holiday rentals

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