
Holiday rentals in Simcoe Island
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Top-rated holiday rentals in Simcoe Island
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Waterfront Casa in wine County w/SAUNA and HOT TUB
Escape to this beautifully updated lakefront home on 170ft of private shoreline in beautiful Prince Edward County. Enjoy our new panoramic view sauna, hot tub and outdoor shower. This relaxing getaway is located on the Bay of Quinte, just 2hrs east of Toronto. A 30 min drive to Sandbanks, 20 mins to Picton/Wellington. Close to many wineries and breweries. Large yard space makes this an ideal home for groups, couples and families looking for postcard views and private spa amenities. ST-2023-0002

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.

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!

Earl View Place - downtown gem!
Enjoy a stylish experience at this centrally located gem, professionally designed and renovated. Compact, elegant and comfortable. The location is amazing, nestled in the historic Sydenham Ward district midway between the downtown area and Queen's University, only a block from Lake Ontario. Earl View Place provides a perfect blend of convenience, comfort and location - get a great night's sleep before heading off to the nearby university, hospitals, or Kingston's many attractions.

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.

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.

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

Hotel Room Bela in downtown Kingston
Welcome to Hotel Room Bela, in the heart of downtown Kingston. Our space is a small and cozy hotel room accommodation with your own private entrance and everything you need for a comfortable stay. We are steps away from unique local stores, restaurants, Queen's University and Hotel Dieu Hospital. Our prime location includes free parking for 1 vehicle. Discounted rate for bookings any day, Sept 25-27, 2026 due to unavailable parking. Licence: LCRL20230000508

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

The Big Dipper - Geo-Desic Dome

Charming and Historic Waterfront Escape in Town

1066 Hastings House

Exquisite Summer Home Retreat with Heated Pool

The Unhurried House

Cozy Loft in Kingston

Tanyas_Place_ygk

Waterfront A-Frame Getaway on Thirty Island Lake
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Long Island Holiday rentals
- Montreal 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
- Thousand Islands National Park
- Wolfe Island
- Pike Lake
- Sandbanks Provincial Park
- Thousand Islands
- Sandbanks Dunes Beach
- Grange of Prince Edward Vineyards and Estate Winery
- Rosehall Run Vineyards Inc
- Lemoine Point Conservation Area
- Kingston 1000 Islands Cruises
- Boldt Castle & Yacht House
- Frontenac Provincial Park
- Closson Chase Vineyards
- Black Bear Ridge Golf Course
- Charleston Lake Provincial Park
- Lake on the Mtn Provincial Park
- Hinterland Wine Company
- Queen's University
- Thousand Islands Winery
- Lake Ontario Park
- Clayton Island Tours
- Casa-Dea Winery & Banquet Hall
- Shorelines Casino-Belleville
- Sandy Island Beach State Park





