Holiday houses in Windlesham

Luxury Gated 3BR Stay in Ascot - By Tempstay

Experience refined living in our exclusive gated apartment in Ascot, perfectly suited for guests looking for style, relaxation and a premium stay in one of Ascot's most desirable locations. Thoughtfully designed with elegant interiors, our stunning three-bedroom, first floor apartment offers a blend of modern luxury and homely comfort. Located within a secure gated development, guests can enjoy bright open-plan living spaces, high-quality finishes, and a stylishly designed interior throughout.

Value · Location · Accuracy

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 · Location · Cleanliness

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.

Family · Location · Sleep quality

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.

Family · Location · Check-in

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 · Location · Kitchen

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.

Location · Family · Sleep quality

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 · Location · View

Bright & Airy Apartment in Charming Sunninghill

Welcome to our chic and cosy 4-sleeper apartment, nestled in the charming village of Sunninghill, Ascot perfect location for the Royal Ascot event. With two stylish bedrooms, an open-plan living area, a fully equipped kitchen, and private outdoor spaces, this is the perfect home away from home for both business and leisure travellers. Whether you’re visiting for Ascot Racecourse, a weekend retreat, or work, you’ll love the comfort, convenience, and thoughtful touches throughout.

Location · Family · Wi-Fi

Self-contained ‘Laurels Lodge’

Kick back and relax in this calm, comfortable, clean, self-contained ‘The Laurels Lodge’. Private parking & own entrance with small decking, table & chairs for alfresco dining. Patio doors open into Living area & kitchenette, smart TV, WiFi. Fully equipped kitchen with fridge freezer, dishwasher, hob, washing machine & all mod cons! Bathroom with shower, one small double bed room & super-king size mattress on sleeping platform accessed by stepladder in the living area.

Location · Family · Getting around

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.

Value · Location · Cleanliness

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.

Location · Value · 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.

Location · Family · Nearby