
Holiday rentals in Simcoe Island
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Top-rated holiday rentals in Simcoe Island
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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

🌙 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.

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; enjoying an evening stroll at sunset; 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!

Stunning Retreat with Sauna and Spectacular Views
A peaceful country retreat with all the little luxuries. Enjoy stunning river views, watching local wildlife and taking in the serenity of the surroundings. Wander the boardwalk to the 60-foot floating dock. Relax in your private sauna or soaker tub overlooking 28 acres of farmland. This craftsman-built cottage is filled with thoughtful details including herringbone tile, reclaimed doors, and custom millwork. Combined with modern comforts, this property is a little piece of paradise.

Shopkeeper's Apartment Waterfront 1186B Main st.
Step onto the deck, soak in the lake and awesome view to Kingston. Just a few steps to the water - this very spacious 2000 sq. ft., vintage appointed, 2 BR, 2 WC, suite is right in the centre of Wolfe Island's village, Marysville. Soaring ceilings, freshly renovated, with pine floors, beautiful views and sunsets, outdoor dining, luxurious linens, our character filled Shopkeeper's Lakeside Apartment is the perfect place while visiting Wolfe Island. Bring your water toys and launch!

The Hideaway Cabin
Welcome to the Hideaway Cabin, where you can unwind in the embrace of nature. Here, you can sizzle your favorites on the grill, lounge in the Adirondack chairs on the balcony, or simply relax indoors. Come evening, gather by the firepit on the porch to watch the fireflies dance or relax in the hot tub on the back porch. It's the ideal blend of natural serenity and homely comfort. In the winter, cozy up by the woodstove in the living room and catch up on your favorite TV shows.

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

Off-grid A-frame cabin, come relax in the forest!
Welcome to “The Hemlock” cabin One of two unique cabins on the property. 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 and wildlife in a peaceful, private setting, relax and unwind by the fire! We look forward to having you!

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.

The Prince Edward County Church, A Unique Escape
Stunning 1888 converted church in Prince Edward County on a private 2.3-acre waterfront property backing onto the Bay of Quinte. This one-of-a-kind stay blends soaring ceilings and historic charm with modern luxury. Sleeps 8 adults with 4 bedrooms, lake views, direct waterfront access, high-speed WiFi, Sonos, fireplaces, kayaks, and more. Featured in Forbes, House & Home & Cottage Life with over 300 guest reviews.
Popular amenities for Simcoe Island holiday rentals
Other great holiday rentals in Simcoe Island

Romantic Yurt - Summer Ready & Unique!

The Big Dipper - Geo-Desic Dome

glamping farm bubble

Sandra's Wee House on Simcoe Island

The Chez Heron. A small gothic castle in Chaumont

The Supernova Glamp Camp THE MOON.

Lakefront with Sauna & Trails

MAPLE | Waterfront PEC Cottage w/ Dock Lake Views
Destinations to explore
- New York City Holiday rentals
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- Newark Holiday rentals
- Mont-Tremblant Holiday rentals
- Buffalo Holiday rentals
- Brampton Holiday rentals
- Cambridge Holiday rentals
- Niagara Falls Holiday rentals
- Sandbanks Provincial Park
- Thousand Islands National Park
- Thousand Islands
- Pike Lake
- Sandbanks Dunes Beach
- Wolfe Island
- Boldt Castle & Yacht House
- Frontenac Provincial Park
- Kingston 1000 Islands Cruises
- Rosehall Run Vineyards Inc
- Queen's University
- Lemoine Point Conservation Area
- Charleston Lake Provincial Park
- Black Bear Ridge Golf Course
- Grange of Prince Edward Vineyards and Estate Winery
- Closson Chase Vineyards
- Bay of Quinte
- Thousand Islands Winery
- Lake Ontario Park
- Westcott Beach State Park
- Lake on the Mtn Provincial Park
- Clayton Island Tours
- Shorelines Casino-Belleville
- Hinterland Wine Company





