Boutique Rentals & Executive Property Management

About Us

We’re committed to providing exceptional property management services and outstanding short & long term rental solutions for travelling executives, actors and film & TV professionals.

Featured Properties

Waverly Road

This 3100 square foot home in the heart of the Toronto Beach area was built in 1908 and has been meticulously renovated and maintained, boasting an all season pool & spa that provides warmth, exercise and relaxation all year long.

Glenrest Drive

A luxury renovated 1950’s cottage compound 1 hour and 20 minutes from Toronto, this property features a natural Canadian made wood-fired hot tub and numerous break out bunkies that are separated from the designer main cottage. Enjoy the “sea-like” expansive shoreline with crystal clear water and waist deep sandy beachfront.

Executive Property Management

Our executive property division is the gold standard of property maintenance. Our clients receive on-demand service, across Ontario.

  • This is the best Airbnb we’ve ever stayed at. The house is amazing, and its owners are outstanding.

    AirBnB Guest, Waverly Road

  • Very relaxing experience. Everything we needed was available at the house as well there were many places for food etc. available within walking distance including the beach. Overall amazing and relaxing place to stay.

    AirBnB Guest, Waverly Road

  • Very comfortable and cozy stay. All furniture and pillows were high end comfort. The pool and spa was nice and cleaned. This is a great stay!

    AirBnB Guest, Waverly Road

  • One of the best Airbnb stays we've ever had. The place was beautiful and spotless. The hosts were amazing at communicating well with us. The lake is magical. we'll definitely come back. Thanks for everything.

    AirBnB Guest, Glenmore Road

  • Nothing overlooked at this lovely cottage! Beautifully decorated, lovely waterfront, tiki bar, fire pit, games…too many extras to mention! Communication A+! Thx so much for sharing your beautiful cottage

    AirBnB Guest, Glenmore Road

Waverly Road

Glenrest Drive

Contact us.

Have a question about our properties? Feel free to reach out, we’d love to connect.

info@chesterhudsonproperties.com

(416) 820-6870‬