Family-friendly holiday rentals in Winkfield Row

Cosy private detached from main house large room

Private air-con (from Oct’26) self-contained garden room with double bed, double sofa bed, WC, shower and separate dressing room. Access to quiet rear garden with seating. On-street parking on quiet residential road. Kettle, microwave, airfryer, toaster, fridge. Wifi, Sky and Smart TV with Netflix. 1.7 miles to Ascot Racecourse, 2 miles to Ascot Station, 4.5 miles to Legoland, 7 miles to Windsor, 9 miles to Thorpe Park. 5 minute drive to Lapland UK. Please message to discuss children’s discount.

Indoor spaces · Kitchen · Hospitality

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.

Family · Kitchen · Quiet

The Brickmaker’s Loft

A newly fitted one bedroom apartment, with living area, full kitchen, large bedroom with king size bed, a full size single bed in the eaves, and an extra single bed if needed. We’ve kitted the Brickmaker’s Loft out with everything you would need. The kitchen has an oven, fridge, dishwasher, kettle, toaster, microwave and all the normal cooking bits, crockery etc. The bathroom has a walk-in shower, loo, and sink, and a washing machine if you need it. The bedroom is a lovely relaxing space.

Indoor spaces · Family · Comfort

Modern home in Sunninghill

Modern open-plan home-from-home in the heart of Sunninghill Village. Welcome to your home-from-home in the heart of Sunninghill, Ascot. This modern, recently refurbished 2-bedroom home is perfect for professionals, couples, and small families needing a comfortable & convenient short stay. There is also space for you to bring a cot bed. The property is just a 2 minute walk from all the amenities that the beautiful village of Sunninghill offers; and closeby is Sunningdale, Ascot & Windsor.

Indoor spaces · Family · Comfort

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 9 mins to Legoland Walking distance to Lambrook School 10 mins to Swinley Forest, Go Ape, MTB bike park 11 mins to Ascot 16 mins to Windsor & Wentworth 30 mins to Henley 1 hour by train to London

Family · Indoor spaces · Heating

Delightful small converted barn

Unique newly converted small barn, bright, light and self contained. Sleeps 3 adults or 2 adults and 2 children (or 2 small adults) due to restricted height space in loft. Large gravel drive behind big, wooden gates for safe and easy parking. An assortment of Teas, coffee & biscuits. The Little Barn is Situated down a country lane, within the garden of the house, walking distance to pubs and restaurants. Near Lapland UK, Legoland, Ascot, Windsor, Train stations to London and Reading

Family · Kitchen · Hospitality

Relaxing home near Legoland, Ascot, LaplandUK

This cosy cottage is situated in Windlesham, a pretty village in the Surrey Heath borough. Situated between Chobham Common and Swinley Forest, it is on the doorstep to some fantastic country walking and cycling routes; not to mention the famous golf courses in the area. Ideal location to visit Legoland, Thorpe Park, Ascot racing and Windsor castle. Heathrow Airport is only 15 miles away. Windlesham is known for the Boxing Day pram race and also a location to amazing gastro pubs.

Indoor spaces · Kitchen · Parking

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.

Family · Indoor spaces · Decor

Hagrid Hut Themed - Hot Tub - Warner Bro Studio

Hagrid & Fang are away and would like you to watch over his home, located next to the Forbidden Forest! This unique Glamping experience is conveniently located only 12 minuets drive from the Warner bros Studio Tour & 40 minuets to central London via Chorleywood Metropolitan line. Hagrid's Hut sleeps five wizards - making it the perfect accommodation choice for families and friends. Soak under the stars in the leaky cauldron wood fired hot tub nestled in nature, MAGIC.

Family · Kitchen · Bathroom

Luxury Penthouse with Huge Balcony

Take a break in our luxurious penthouse. The enormous south-west facing balcony offers panoramic views of the sunset each evening, making it the perfect spot to relax after a day. The interior is bright and modern, with floor-to-ceiling windows and sliding doors that fill the space with natural light. The fully-equipped kitchen has everything you need to prepare meals, and the living room is outfitted with premium audio (Sonos) and TV for your entertainment.

Family · Kitchen · Bathroom

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.

Kitchen · Indoor spaces · Layout

The Cottage

Welcome to our charming 3-bedroom cottage, nestled in the tranquil beauty of Chobham Common. If you're seeking a peaceful escape with a touch of rural charm, you've found your perfect retreat. Despite our idyllic rural setting, you're only a short 25-minute train ride away from the vibrant heart of London. Experience the best of both worlds – the tranquility of the countryside and the excitement of the city.

Indoor spaces · Kitchen · Quiet