Quietly considered places to stay and call home
About the Group
Chesterfield Property Group is run by Harriet & Ryan — two full-time teachers with a shared love of renovating properties and turning them into wonderful places to stay. What began as one Victorian conversion in Windsor has grown into a small, deliberately chosen portfolio, held to the same standard throughout.
We believe good property is about restraint, not scale: fewer homes, cared for properly, with the details — linen, lighting, a proper coffee machine — chosen the way we'd choose them for our own front door. We live locally to both properties, so help is always close by.
The Windsor Home
A short walk from the castle and the river, our Windsor apartment is available to book directly through Airbnb — period charm, considered interiors, and a peaceful residential street in the Golden Triangle.
The Changing of the Guard passes right through town — a two-minute walk from the front door
Set on one of Windsor's most desirable streets in the sought-after Golden Triangle, our ground-floor Victorian conversion has its own private entrance through a newly fitted period front door. Inside: a compact fitted kitchen with Nespresso machine, a two-seat dining table, and a cosy living area with a 40" Smart TV built into a bespoke media wall. The bedroom has a comfortable double bed with bedside USB charging, and the bathroom a proper walk-in shower.
On arrival we leave a welcome hamper from the Windsor Farm Shop, along with milk, tea, coffee and granola — and we offer early check-in and late check-out whenever we can.
Guest Favourite · 83 reviews · Hosted by Harriet & Ryan
On your doorstep
Heathrow is a 20-minute drive, and both Windsor rail stations are within walking distance for easy trips into London. Free parking is a short drive away, with secure paid parking just around the corner.
Check dates & book on Airbnb →The Ascot Home
Our Ascot property is currently home to a long-term tenant and isn't available to book — we're glad to show it here as part of the wider Chesterfield collection.
A well-proportioned family home in one of Berkshire's most sought-after villages, currently let on a long-term basis. Managed with the same care as every Chesterfield property.
Currently let and managed by Chesterfield Property GroupGuest Reviews
Real ratings from the Windsor apartment's Airbnb listing — 83 reviews, updated live.
83 reviews
92% of guests gave 5 stars, 8% gave 4 stars — no review below 4 stars. Read every individual review, written by guests, directly on Airbnb.
Read all 83 reviews on Airbnb →For Landlords
Chesterfield Property Group is a Berkshire-based property management company with over 10 years' experience managing, renovating and looking after residential properties. We help landlords maximise their investment through professional property management and luxury short-term accommodation — delivering exceptional guest experiences and hassle-free ownership.
Local expertise, personalised service.
Stay in one of our exclusive Airbnbs.
Into a money-making property.
Our promise to you.
We can pay you, improve your property, and manage it for you.
Looking for a new management company? Need help renting your property out? Let us pay you and turn it into a luxury Airbnb.
Get in touch today so you can enjoy the results.
Enquire about property management →
