
Holiday rentals in Simcoe Island
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Simcoe Island
Guests agree: these stays are highly rated for location, cleanliness and more.

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.

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.

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.

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.

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

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!

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

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.

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

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.

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

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
Other great holiday rentals in Simcoe Island

Lennox Place

Bright & Modern 2BR Suite | Rustic Bar + Parking

Nature Getaway in Luxury Yurt - Super Warm & Cozy!

Lakefront with Sauna & Trails

Sunset Cottage on Lake Ontario at Pillar Point

The Chocolate Suite

Sunset Cottage

The Fig and Fox, 1858. Cape Vincent, New York.
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Long Island Holiday rentals
- Greater Toronto and Hamilton Area Holiday rentals
- Greater Toronto Area Holiday rentals
- East River Holiday rentals
- Mississauga Holiday rentals
- Hudson Valley Holiday rentals
- Philadelphia Holiday rentals
- Pocono Mountains Holiday rentals
- Island of Montreal Holiday rentals
- Bay of Quinte
- Thousand Islands National Park
- Wolfe Island
- Pike Lake
- Thousand Islands
- Sandbanks Provincial Park
- Kingston 1000 Islands Cruises
- Rosehall Run Vineyards Inc
- Lemoine Point Conservation Area
- INVISTA Centre
- Boldt Castle & Yacht House
- Sandbanks Dunes Beach
- Closson Chase Vineyards
- Charleston Lake Provincial Park
- Frontenac Provincial Park
- Hinterland Wine Company
- Grange of Prince Edward Vineyards and Estate Winery
- Lake on the Mtn Provincial Park
- Queen's University




