Holiday houses in Winkfield

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Top-rated holiday rentals in Winkfield

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Top Guest favourite

An open-plan kitchen and living area features a wooden countertop with bar seating. The room is illuminated by natural light from the skylight, highlighting the contrasting blue and white walls. A cozy sofa and decorative artwork create a welcoming space.

Guesthouse in Windsor

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!

LocationFamilyAccess

4.94 out of 5 average rating, 208 reviews

Superhost

The exterior of the stylish barn conversion is showcased, featuring a well-maintained garden area with a stone patio and outdoor dining set. Lush greenery surrounds the property, while large windows provide a view into the inviting interior. The sky is partly cloudy, enhancing the serene atmosphere.

Barn in Winkfield

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

FamilyLocationQuiet

4.73 out of 5 average rating, 15 reviews

Top Guest favourite

The charming Victorian Lodge features a classic brick exterior with white trim, framed by lush greenery. Two inviting front windows and a central doorway are surrounded by decorative flower pots. A gravel pathway leads to the entrance, highlighted by an expansive tree nearby.

Cottage in Old Windsor

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.

FamilyLocationCheckout

4.99 out of 5 average rating, 110 reviews

Top Guest favourite

The charming exterior of a Victorian terraced home features a white door framed by climbing greenery. Flower boxes filled with pink and white blooms adorn the windows, while a small bench sits beneath a decorative wrought iron fence.

Cottage in Bray

Charming terrace in the heart of Bray village

Our lovely victorian terraced home is perfectly situated for all the fine dining that the charming village of Bray has to offer. The Michelin 3-starred Waterside Inn and Fat Duck are a few mins walk away as are the Crown Inn, Hinds Head and Caldesi. Stroll 15 mins more and you’ll find the recently renovated Monkey Island Estate. A short drive and you can be at either Ascot or Windsor Races, Cliveden House, Legoland, the village of Cookham or the beautiful river Thames towns of Marlow or Henley

ValueLocationAccess

4.95 out of 5 average rating, 169 reviews

Guest favourite

A cozy sleeping area features a spacious bed dressed with a soft, textured blanket. Two decorative pillows sit at the head of the bed. Nearby, a charming chair complements the rustic wooden beams that arch overhead, adding character to the room.

Condo in Bracknell Forest

The Hayloft Suite, St Michaels Grange

The hayloft is a self contained 1-bed beautiful quirky addition to a private family home in a courtyard, secure in a gated environment, close to Bracknell centre but giving the feel of being in the country. A lovely place to relax, and enjoy the pub down the road after a days work. Perfect for anyone working in Bracknell from time to time or on a weekly basis who wants to feel more at home when away. Tea, coffee, milk, porridge pots and welcome treats included. Easy parking outside your door.

FamilyLocationQuiet

4.92 out of 5 average rating, 290 reviews

Top Guest favourite

A cozy sitting room is featured, showcasing a comfortable armchair and a large coffee table adorned with various books and decorative items. A warm fire burns in the fireplace, and built-in shelving lines one wall, filled with a diverse selection of books.

Cottage in Bracknell Forest

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

ValueFamilyComfort

4.97 out of 5 average rating, 370 reviews

Guest favourite

Home in Berkshire

Luxury Villa with Hot Tub - Royal Ascot, Legoland

Welcome to Mayfield Place – a spacious, stylish and elegant home nestled in the quiet village of Winkfield, just a short drive from Windsor and Ascot. Perfect for families or groups of friends - this beautifully designed 6 bedroom property (4 bedrooms in the main house with a connecting door to a 2 bed annexe, secondary kitchen, bathroom and lounge area). A stunning landscaped garden, multiple living areas & statement bedrooms make this the ideal base for weekend getaways or longer stays.

LocationFamilyHot tub

4.93 out of 5 average rating, 14 reviews

Guest favourite

A charming exterior of the converted barn is framed by lush greenery, featuring a wooden deck and double doors. A cozy outdoor seating area with wicker chairs and a table is surrounded by an assortment of potted plants and flowers, enhancing the tranquil garden setting.

Barn in Bracknell Forest

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

FamilyValueGetting around

4.91 out of 5 average rating, 918 reviews

Top Guest favourite

A charming self-contained cottage is set within a lush private garden, characterized by brick exterior and a slate roof. A welcoming door leads to the entrance, framed by greenery and flowering plants, with a spacious lawn surrounding the building.

Cottage in Sunninghill

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.

ValueLocationAmenities

4.96 out of 5 average rating, 883 reviews

Guest favourite

A spacious garden is presented, featuring a neatly manicured lawn with patches of greenery. The exterior of the apartment is visible, showcasing a white façade with multiple gabled roofs. A patio area is seen on the left with outdoor furniture, while trees provide a natural backdrop.

Guest suite in Bracknell

4 people beautiful views near Legoland & Lapland

Lovely, 2-bed modern apartment, fantastic views over the gardens. Spacious apartment for 4 people in a quiet countryside setting, 1.5 miles to the Lexicon town centre & excellent shops, entertainment, eating, cinema. 5 miles to Legoland, 3 miles to Ascot (the races). 50 minutes into London Waterloo or Paddington from Maidenhead in 18 minutes. 2 x 4k TV's, Disney, Netflix and SNES mini

ValueFamilyCondition

4.96 out of 5 average rating, 142 reviews

Guest favourite

Home in Sunninghill

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.

LocationOutdoor spacesBathroom

5.0 out of 5 average rating, 7 reviews

Guest favourite

The studio features a comfortable double bed with two decorative pillows and a light blanket. Shelving units are positioned on either side, with hanging space above. A soft couch, adorned with a striped cushion, is situated in front. Soft lighting enhances the serene ambiance.

Guest suite in Bracknell

Modern studio apartment in Warfield, Bracknell

Self-contained studio annexe in a quiet cul-de-sac with comfortable double bed, kitchen area, shower room, lounge area and private entrance. Plenty of street parking available. Free WiFi access Breakfast: tea/coffee/milk/cereals/bread and preserves provided to set you up for your day :-) Iron/ironing board/airer provided

FamilyValueParks

4.96 out of 5 average rating, 135 reviews