Holiday rentals in Simcoe Island

5 out of 5 average rating, 214 reviews

Houseboat in Yarker

4 season cabin in the woods -A romantic Riverboat!

You won’t forget this memorable experience! A 1974 River Boat has been lovingly transformed in to a whimsical all season cabin. Come for the fantasy then bask in the comfort and romance of it. Luxurious amenities include everything but the kitchen sink..literally! A perk to no running water is that I do your dishes at my place while you relax! The houseboat is tucked in to the trees and just across the road from a lakefront park. Plus...a Playshed full of seasonal outdoor equipment is included!

4.9 out of 5 average rating, 145 reviews

Home in Kingston

Stay & Shop The Boho Room Entire 3 Bed, 1 Bath

Private entrance to a spacious 3 bedroom, 1 bath with kitchenette & small living room. One Parking Spot. 4 minute drive from Airport & 15 minute drive to downtown core. Kingston has always been a makers town where arts culture runs deep; visit the limestone city while occupying one half of a makers house. The Boho Room is a textile & handcrafted goods company that has grown into an Airbnb experience. Filled with woven wall hangings & nostalgic art prints, you are always welcome to stay & shop.

4.97 out of 5 average rating, 133 reviews

Cottage in Hammond

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 house in Township Of Frontenac Islands

4.98 out of 5 average rating, 130 reviews

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.

5 out of 5 average rating, 105 reviews

Guest suite in Kingston

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!

4.98 out of 5 average rating, 139 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

4.91 out of 5 average rating, 191 reviews

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

4.83 out of 5 average rating, 162 reviews

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.

4.92 out of 5 average rating, 474 reviews

Townhouse in Kingston

Downtown Two Bedroom Apartment With Parking

This 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 second floor of a duplex, consists of a large open concept living space along with two bedrooms and a bathroom. Licensed for short term rental with the City of Kingston - License #LCRL20240000006

Superhost

Home in Kingston

4.91 out of 5 average rating, 149 reviews

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.

5 out of 5 average rating, 118 reviews

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.