Holiday rentals in Woodside

Windsor Home with Free Parking

Welcome to our 1-bedroom, skylit, guest house with off-road parking & private patio. Located in a quiet cul-de-sac close to Legoland, Windsor Racecourse, and Windsor Castle, our home is the perfect retreat after a long day of sightseeing. The bedroom can be set up with either a kingsize bed or 2 singles on request, while the sofa bed can comfortably fit 2 people. Our family run Airbnb is a great fit for families with kids, a couple or a small group of friends. Any questions, please just ask!

Luxury 4 Bed Barn, 10 Mins to Windsor

Uncover the charm of a stylish barn conversion located just 10 minutes from Windsor. Featuring a spacious, well-designed layout with an inviting reception hall and an elegant galleried landing, this exceptional retreat seamlessly combines relaxation with comfort. Set amid picturesque countryside, it’s perfect for a peaceful escape or a longer stay. This property combines elegance and enjoyment with a range of outstanding features. The open-plan design, with mellow, exposed brick walls, creates

Gorgeous CountryCottage overlooking Windsor Castle

The Victorian Lodge (1876) is a charming & quintessentially English country cottage on a private estate once owned by King Henry 8th. It sits right beside Windsor Great Park, at the entrance of a long driveway to Little Dower House, where the owners of the Lodge live. The private gardens and stunning view at the Victorian Lodge provide the perfect setting for a small intimate wedding. Whilst the romantic gardens within the Little Dower House estate provide an ideal venue for larger weddings.

Garden Studio

An entirely self contained base with underfloor central heating if required. A king sized bed and en suite shower room. Pillows and duvets are hypoallergenic, and all bedding pure cotton. A kitchenette with microwave, toaster, kettle and fridge. Ultra-fast full fibre Internet access, and TV for all Freeview channels and Netflix. The historic Thatched Tavern pub with wide-ranging menu is within easy walking distance. Please observe a strict no smoking, vaping or candles rule in the studio.

Ascot Annex

A self-contained, 2 bedroom, 3 bed, 1 bathroom Annexe, next to our main house, in an idyllic hamlet in Ascot. The property has its own private entrance. The space is self-catering with a kitchen and has a dining space to seat 3 comfortably, along with a sofa and a smart TV Netflix included. 5 minutes to Legoland 7 minutes to Ascot Station 4 minutes to Ascot Racecourse 10 minutes to Windsor Castle and Wentworth 15 minutes to Bray and Longcross Studios. 25 minutes to Pinewood Studios

2 Bedroom Luxury Cottage (Secure & Quiet)

This charming Cottage is located in the picturesque Village of Englefield Green. Just four miles from Windsor Castle, three miles from Wentworth Golf Course and six miles from Ascot Race Course. Heathrow Airport if just six miles away. 300 metres further down the lane is The Royal Air Force Memorial and below that, on National Trust grounds that skirts the River Thames is the Magna Carta Memorial. The Royal Holloway University is a ten minute stroll across the Village.

Luxury 2 bedroom cottage

Luxury Cottage at Hayley Green A charming, character-filled retreat for up to 4 guests in a peaceful semi-rural setting. Designed for comfort and relaxation, it’s ideal for couples, families, or friends. Enjoy a well-stocked library if you prefer to stay in. Perfectly located: 6 mins to Lapland Ascot 9 mins to Legoland 11 mins to Ascot 16 mins to Windsor & Wentworth 30 mins to Henley-on-Thames Under 1 hour by train to London via nearby Bracknell station

The Old School House, Ascot, Berkshire

Beautiful small self-contained character cottage set within private garden, one mile from Ascot. Open plan studio room with sitting area, kitchenette and bedroom area; en suite shower room/WC. Perfect for 1-2 adult guests looking for a comfortable and relaxing place to stay, whether for business or pleasure. It is ideal for visitors to Ascot Races, Windsor, close to Heathrow and a lovely rural retreat less than one hour from central London.

Flat 4, Luxury Apartment Near Ascot Racecourse

A Stunning contemporary first floor apartment is the perfect spot for exploring the local area including Ascot Races, it is close to Wentworth, Sunningdale & The Berkshire Golf Courses. Walking distance to the racecourse, restaurants, bars/cafes. The Apartment has access to a beautiful landscaped garden. There is parking at the property for 1 car. The property is also within a 10 minute drive to Windsor & 5 mins to local Polo clubs.

The Coach House

Set minutes from Windsor Great Park, The Coach House is a quiet studio retreat with its own front door. King-size bed downstairs, loft single upstairs - it sleeps three - plus kitchen, en-suite shower room and driveway parking with room for a work van. A few minutes' drive from Ascot High Street and Racecourse, Windsor and Legoland, with Wentworth, Guards Polo and Lapland UK close by. The Thatched Tavern pub is a five-minute walk.

Luxury Wentworth Retreat. 3 Bed by the Golf Course

Set within the prestigious Wentworth Estate, this luxury 3 bedroom, 2 bathroom apartment offers refined living just moments from the fairway. Stylish interiors, spacious open plan living, and a high end finish throughout create the perfect setting for both relaxing stays and entertaining. Ideal for golf getaways, corporate bookings, or weekend escapes, this is premium Surrey living at its finest.

The Royal Paddock

A beautiful townhouse on the edge of Royal Ascot Racecourse. Experience the elegance and excitement of Royal Ascot from your own private haven. The Royal Paddock is a three-bedroom, three-bathroom townhouse that quite literally backs onto the world-famous Royal Ascot Racecourse, offering a unique blend of luxury, comfort and British charm.