
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

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.

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

Newly renovated downtown suite!
Downtown Sydenham Ward… Location… Location… Location! Stay with Whit and enjoy a newly renovated private suite in a 1930’s downtown Sydenham Ward home. Enjoy your own private entrance to a spectacular lower level suite. One luxurious queen bed with top-of-the-line bedding, upgraded double pull-out sofa, three-piece bath, electric fireplace, large screen TV (Netflix, etc.), and kitchenette. This property is perfect if you’re looking for a quiet escape, parking included!

Spacious and brightly furnished lower unit
Bright, clean and cozy - we are a respectful family of 3, and welcome you for your stay. This area is ideal for those who like to keep to themselves, with a private bedroom, kitchen, and living room. It can be entered directly from outside. Included with two stylish pull-out couches (can be turned into beds), an open kitchen provided with cooking utensils and equipment, protected with outdoor security cameras, as well as a washing machine to take care of dirty laundry.

Bright, cozy basement apartment with fireplace!
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

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

The Sweet Suite
- This bright, peaceful and quiet private apartment has an abundance of amenities at your home away from home. Enjoy this space and explore what Kingston has to offer from its convenient central location. - Separate exterior entrance. - Sound treated ceilings and walls. - Beautiful wooded area, park, and walking paths behind the property. - Two tobogganing hills -Complimentary snacks. -Linens washed after each stay with o3 commercial grade laundry system

Downtown Haven: Roomy Home with Parking
This newly renovated home is located in downtown Kingston, minutes walking distance to major amenities such as the K-Rock Centre, waterfront, restaurants, bars, and shopping on Princess Street. The unit, which encompasses the entire first floor of a townhouse, consists of a large open concept living space along with one bedroom and a bathroom. Fully licensed for short term rentals with the City of Kingston - License #LCRL20230000420

Bachelor Apt close to Queen's/Downtown Kingston
This third-floor apartment is VERY close to Queen’s University as well as Lake Ontario and historic downtown Kingston. It has its own private entrance at the back of the house up a set of outdoor, narrow, metal stairs (the original fire escape). It also has air conditioning. The homeowners live on the first two floors, making this the ideal space for someone looking for a quiet space close to Queen's and downtown Kingston.

Hotel Room Bela in downtown Kingston
A small and cozy hotel room accommodation with a private entrance to your own space and free parking until check out, located in downtown Kingston's Sydenham Ward. You are steps away from the heart of downtown shopping, restaurants, Hotel Dieu Hospital and 3 blocks from Queen's University and KGH. Our space is small at 175 sq ft, but you’ll have everything you need for a comfortable stay. Licence: LCRL20230000508

KingstonStays | Historic Downtown Hideaway
Your historic hideaway awaits you with a calming, cozy luxury. It is in the heart of downtown Kingston within easy walking distance to Market Square, the Wolfe Island ferry, the Leon's Center, Fort Henry, Confederation Park and City Hall, both Hotel Dieu and Kingston General Hospitals, Queens University, RMC as well as all of the restaurants, cafés, bars and shops the beautiful Canada's first capital has to offer.
Popular amenities for Simcoe Island holiday rentals
Other great holiday rentals in Simcoe Island

Downtown Kingston Apartment

Earl View Place - downtown gem!

Waterfront home, beautiful Simcoe Island getaway

Cosy bedroom with flexible check in/out times

Tree top views and exposed beams.

Cozy Studio in Sydenham Village

New modern studio apt

BigSunnySuite in Grand Country House, WiFi Utils
Destinations to explore
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- Thousand Islands National Park
- Wolfe Island
- Black Bear Ridge Golf Course
- Selkirk Shores State Park
- Thousand Islands
- Brockville Country Club
- Tremont Park Island
- Southwick Beach State Park
- Sydenham Lake
- Otter Creek Winery
- Dry Hill Ski Area
- Grange of Prince Edward Vineyards and Estate Winery
- Traynor Family Vineyard
- Closson Chase Vineyards
- Hinterland Wine Company
- Casa-Dea Winery & Banquet Hall
- Rosehall Run Vineyards Inc