Holiday houses in Woodside

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Top-rated holiday rentals in Woodside

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite

A spacious living area features a comfortable sectional sofa adorned with colorful throw pillows. A light rug defines the seating space, while natural light filters through large windows. Minimalist decor elements, including a mounted antler and lanterns, add character to the neutral-toned walls.

Home in Englefield Green

4.97 out of 5 average rating, 142 reviews

Five Star Boutique House near Windsor Castle, Ascot & London

This Grade 11 listed Mews property was built in 1872 and offers contemporary, luxurious living space. Luxurious king size beds, beautiful bathrooms, abundant art and character; the properties look onto an ancient courtyard with fountain, secure behind private gates with parking. The location is exceptional. Windsor Great Park is a 10 min stroll away, and Windsor is 3 miles away, Wentworth Golf Club and Ascot are all within 6 miles. Central London is 35 minutes by train. Heathrow is 6 miles away.

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Superhost

Cabin in Bray

5.0 out of 5 average rating, 3 reviews

The LEGO Themed Lodge & Petting Farm near Legoland

Up to 4 adults max-No adults in our Lego bunk beds! Make some forever memories at the unique family-friendly Willow Court Farm. Enjoy our refurbished 2 bed room Lego Themed Lodge perfectly positioned only 8 mins from Legoland & Windsor town and only 15 mins from Lapland Ascot. We also have a small petting farm on site all year round with pygmy goats, sheep, pigs, rabbits, chickens, ducks and guinea pigs . Guests can even collect their own fresh complimentary eggs from the hen house nest box.

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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

4.94 out of 5 average rating, 203 reviews

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!

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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

4.99 out of 5 average rating, 110 reviews

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.

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Guest favourite

A detached structure, set against a backdrop of trees with autumn foliage, features a double garage below and a private entrance. The brick facade is complemented by a roller shutter door and a pathway leading to the entrance, conveying a sense of privacy and space.

Guest suite in Sunninghill

4.94 out of 5 average rating, 17 reviews

Ascot Annexe

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

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Top Guest favourite

A cozy living area features a comfortable white sofa adorned with striped cushions. Natural light filters through two windows with shades, highlighting a wooden coffee table and side table displaying a small vase of flowers. A mirror reflects the space, adding depth.

Cottage in Englefield Green

5.0 out of 5 average rating, 392 reviews

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.

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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

4.97 out of 5 average rating, 364 reviews

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

ValueFamilyLong stay

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

4.96 out of 5 average rating, 879 reviews

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.

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Guest favourite

Guesthouse in Sunninghill

4.93 out of 5 average rating, 91 reviews

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.

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Top Guest favourite

Condo in Windsor

4.94 out of 5 average rating, 205 reviews

Modern Windsor home with free off-street parking

Welcome to our stylish, child-friendly 2-bed apartment in central Windsor! Ideal for families, couples, or a business stay. Just a short walk to Windsor Castle, shops and the train station. Legoland and Lapland UK are also closeby, plus there's easy access to London and Heathrow. Enjoy free parking, fast Wi-Fi, a fully equipped kitchen, and a spacious living area—perfect for relaxing after a day out.

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Guest favourite

The spacious living area features high wooden beams and large windows that allow ample natural light. A fireplace is centrally located, framed by a mix of comfortable seating and a glass coffee table. A staircase leads to the upper level, enhancing the open design.

Barn in Buckinghamshire

4.92 out of 5 average rating, 114 reviews

Dorney/Windsor Family Getaway with Hot Tub

Unwind with your entire family in our breath-taking barn, brimming with personality and allure. Nestled in a tranquil rural village, it offers access to two charming pubs and a plethora of picturesque countryside and river trails. Just a short drive away, the renowned destinations of Windsor and Eton await, inviting you to immerse yourself in their famed landmarks and rich historical architecture.

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Guest favourite

Home in Sunninghill

5.0 out of 5 average rating, 7 reviews

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.

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