Holiday houses 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.

Location · Value · Heating

Top Guest favourite

Guest favourite

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.

Location · Family · Indoor spaces

The White Room

Welcome to our charming garden room a stone's throw away from the world-renowned Ascot Racecourse! Our cozy and comfortable garden room is the perfect place for those looking for a peaceful retreat in a beautiful setting. Our location is unbeatable - between Ascot Racecourse and the popular Royal Foresters pub, making it the perfect place to stay for those attending the races. We are close to many other local amenities including Windsor Castle, Legoland and the beautiful Virginia Water Lake.

Value · Location · Bathroom

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.

Location · Family · Laundry

Delightful Period House with Sauna & Games Tables

Wonderful, spacious, peaceful, unique large Period property. Plenty of parking space. Perfect for families, friends gatherings and business trips and dogs as enclosed garden. Equipped with a large 5-6 person infra red sauna, 4ft Table Football; 5ft Air Hockey and 6 ft Table Tennis tables. Early 1900’s large Cottage, fully refurbished with all mod cons but decor in keeping with the period. Near to all amenities and some marvellous places to visit, but in a peaceful location.

Family · Location · Nearby

Top Guest favourite

Guest favourite

Luxury 4 bedroom cottage near Guildford, sleeps 6

A self-contained cottage situated in a quiet position surrounded by woodland within 4 miles of Guildford town centre and refurbished to a high standard with fully equipped kitchen and a utility room with washing machine, tumble drier and downstairs toilet. There are four bedrooms , one ensuite and family bathroom. Parking for 3 cars. Large garden with patio and seating and large netted trampoline for use at your own risk. People from all backgrounds are welcome in our home.

Family · Value · Indoor spaces

Top Guest favourite

Guest favourite

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.

Value · Location · Heating

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.

Value · Location · Decor

Top Guest favourite

Guest favourite

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

Location · Value · Nearby

Top Guest favourite

Guest favourite

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.

Value · Location · Hiking

6 Bedroom Bungalow Ascot Racecourse 75" TV

Modern, spacious bungalow with open-plan kitchen, dining area, and 75" smart TV. Features 5 bedrooms in the main house, plus a private ensuite outhouse when booked for 11+ guests. Newly renovated and ideal for families or groups. Private parking for 4–5 cars. Just 5 mins to Royal Ascot, 15 mins to LEGOLAND, 20 mins to Windsor Castle, and 35 mins to Thorpe Park. Ascot Station is 5 mins away with direct trains to London Waterloo in 45 mins.

Family · Value · Decor

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.

Location · Hospitality · Amenities