Vacation rentals in Windlesham

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Adorable 1 bedroom guest house in Chobham

Separate Annexe, with its own entrance. Peaceful location but in the heart of Chobham Village. Perfectly situated with all amenities in a few minutes walk. We have two great pubs with the White Hart opposite & the Sun Inn just a moments walk up the road. There’s a Coop & a small Tescos for any essentials, along with restaurants on the doorstep! Great walks nearby with Chobham common & a beautiful old Church. Spacious room & luxurious en-suite. Comfy Kingsize bed & sofa which can be a single bed

We Stay - Hills End Cottage with Golf Course Views

Hills End Cottage is part of We Stays’ multi-award-winning collection. An exclusive home in the heart of Ascot, renowned for its prestigious racecourse, Royal Ascot, high fashion and aristocratic tradition. This exquisite cottage has been brought to life with hand-selected furnishings that exude timeless elegance. Among its standout features are a beautifully landscaped garden that backs onto the iconic Sunningdale Golf Course, a home gym and a luxurious open-air bath and rainfall shower for th

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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 Friendly 4BR House w/ Netflix*Play Room

Our spacious 4BR is perfect for families and groups! Downstairs, the open plan kitchen dining provides ample space for everyone to gather. The conservatory doubles as a play area for the kids. There's a convenient small double room with en-suite downstairs. Upstairs you'll find a Super king-size bed , King size bed room, 1 Small double bed and a family bathroom. With a dedicated workspace, high-speed wifi, and Smart TVs with Netflix included, you'll have everything you need to work and play.

Large, Newly Renovated Flat in Charming Village

Welcome to our newly refurbished apartment, in the charming village of Sunninghill, only a short distance from the bustle of Ascot. A 1000 sq feet of living space: two generously sized bedrooms, with king size beds, two beautiful bathrooms, open-plan living area, and fully equipped kitchen, all finished to a very high spec. Plus the benefits of a delightful outdoor patio and lawn area with table and chairs. Great location for Windsor, Legoland, Ascot races and many fabulous golf courses.

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.

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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

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Character studio apartment in the heart of Chobham

Hosted by Elaine, an artist, printmaker, and jeweller. With easy links to London, the apartment is self contained and has ample amenities, comprised of a double bedroom with king bed and bedroom suite, a shower room and kitchen/diner leading to the patio, where there is a table and chairs for outdoor dining. The kitchen has a washer, cooker, fridge/freezer, microwave, toaster and kettle. There is a television, wifi access, comfortable chairs and a sofa bed. Parking for medium sized car.

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.

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Sunny Cozy Stay

Escape to our charming Airbnb amidst a picturesque garden. This one-bedroom retreat offers breathtaking views and modern amenities including a dedicated work space and a spacious dressing room ensuring an organized stay. Enjoy the en-suite bathroom and well-equipped kitchen for delightful meals. Relax in the cozy living room with a book or your favorite shows. Outside, stroll through vibrant garden and bask in the sunlight. Perfect for a romantic getaway or solo retreat.

Stylish 3-Bed Bungalow with garden & parking

This beautifully refurbished 3-bed bungalow offers spacious living with off-street parking for several cars and a private garden with patio. Each bedroom features a super-king bed (or twins), alongside a modern kitchen and a cosy lounge with smart TV. Just a short walk to village pubs and shops, and minutes by car to Lapland UK, Ascot, Sunningdale, Windsor and Wentworth. Perfect for families, professionals, or anyone looking for a comfortable, well-located stay.

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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.