Holiday rentals in Windlesham

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Top-rated holiday rentals in Windlesham

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Guest favourite
Flat
4.95 out of 5 average rating, 19 reviews

Spacious, Newly Renovated Flat in Charming Village

Welcome to our bright and airy, newly refurbished apartment, nestled in the charming village of Sunninghill, and only a short distance from the bustle of Ascot. With two generously sized bedrooms (and two beautiful bathrooms), an open-plan living area, and fully equipped kitchen, finished to a high spec. Whether you're visiting Ascot racecourse, playing golf at one of the world class local courses, or spending a long weekend sight seeing in Windsor - this apartment provides the perfect base.

Top guest favourite
The living area features high wooden beams and a large window allowing natural light. A comfortable sofa is placed alongside classic armchairs. A kitchen area with cabinetry is visible, complemented by a decorative lamp and houseplants. Soft textures enhance the cozy environment.
Cottage
4.99 out of 5 average rating, 106 reviews

Beautiful oak barn in peaceful countryside setting

Delightful detached barn crafted from French oak in a peaceful private lane on a gated country estate. Luxuriously appointed with full facilities for a short break or longer stay. Air Con. Free EV charging point. Many public footpaths close by. Local shops are only a 10 minutes stroll. Gastro pubs, restaurants and independent shops within easy walking distance. A short drive from M25 (J11). Fast rail links to London from Woking. LGBTQ+ friendly. Friendly Spaniel and Siamese cat on site.

Guest favourite
The open-plan living and dining area features a spacious gray sofa paired with a glass coffee table and a wooden dining table with two benches. A TV is mounted on the wall, complemented by elegant decor and natural light from large windows.
Flat
4.86 out of 5 average rating, 81 reviews

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.

Guest favourite
A spacious studio interior is depicted, featuring a blue sofa and a light wooden table. A large flat-screen TV is mounted on the wall, with a white shelf unit nearby. The kitchen area is observed in the background, equipped with bar stools and modern cabinetry. A comfortable bed is positioned in the corner.
Guest suite
4.95 out of 5 average rating, 42 reviews

A contemporary space close to Sunningdale station

The Studio is a self-contained purpose built space completed in 2020 . It is spacious and is furnished and equipped to a high standard. There is a new high quality super king bed. In the kitchen area is an oven/microwave and an induction hob. The shower/WC is compact but very well appointed with high quality fittings. The TV is a large flat screen and there is ample crockery and kitchen etc for two people. Guests can use the terrace which catches the sun from morning to late afternoon.

Guest favourite
A modern open-plan kitchen features dark cabinetry with warm lighting. A white countertop provides contrast, while a small dining table and two chairs are visible. A decorative fireplace adds charm to the space, complemented by a cozy seating area with a coffee table.
Cottage
4.81 out of 5 average rating, 112 reviews

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.

Guest favourite
A spacious lounge features a comfortable gray sofa with decorative cushions. A modern black television is mounted on the wall, reflecting natural light from the nearby entrance. A minimalist marble coffee table sits at the center, enhancing the room's contemporary feel.
Flat
4.98 out of 5 average rating, 125 reviews

Luxury contemporary Apartment

This stylish place to stay is perfect for golf/racing breaks. Sunningdale GC is 5 minutes walk away, Wentworth GC & Ascot Race Course a 5 mins drive. Whilst Windsor Great Park is only 10 mins in the car. All modern appliances including an air fryer. Private barrier parking. Coffee shops and places to eat & drink on your doorstep. Central London is only 40 mins by train from Sunningdale station which will only take you 5 mins to walk to. All in the heart of beautiful Sunningdale.

Top guest favourite
The living area features a cozy two-seater sofa paired with decorative cushions. A textured rug lies beneath. The kitchenette is equipped with modern appliances, including a fridge and a sleek countertop. Natural light illuminates the space through the open patio doors.
Guest house
4.98 out of 5 average rating, 46 reviews

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.

Guest favourite
A serene bedroom is presented with a spacious bed covered in light bedding. A desk with a comfortable chair is positioned nearby, accompanied by a lamp. Natural light streams through the large window, which offers views of greenery, enhancing the tranquil environment.
Flat
4.91 out of 5 average rating, 44 reviews

Elegant homestay in Sunningdale

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.

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
4.98 out of 5 average rating, 298 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

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
4.96 out of 5 average rating, 815 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.

Top guest favourite
A lounge area features a spacious sectional sofa adorned with decorative pillows. A light-colored coffee table sits in front, complementing the neutral-toned carpet. Natural light enters through a nearby window, and a sleek mirror reflects a modern ambiance.
Barn
4.96 out of 5 average rating, 107 reviews

Cosy Garden Cabin

Located in the centre of Bagshot Village this self contained garden building is ideally located as a base to stay whilst visiting surrounding attractions. The cabin has 1 bedroom with a double bed Ensuite shower room. Lounge/kitchen area with sofa, TV, Fridge, Washing Machine, Dishwasher and electric Hob. Windsor is approx 20 mins away by car. Ascot is approx 10 mins away by car. Bagshot Station is a 10 minute walk away

Top guest favourite
A charming brick exterior of a studio annexe is surrounded by lush greenery. Tall trees and various plants create a serene atmosphere. The building features multiple windows that allow natural light to enter, highlighting the inviting architecture.
Guest suite
4.96 out of 5 average rating, 115 reviews

Self contained studio annexe

The Haven is a fully equipped, self catering, double bedded studio annexe, situated in Sunninghill Ascot. It is welcoming, cosy and warm making it a superb place for short term living. Wifi, linen and off-road private parking are included.

Popular amenities for Windlesham holiday rentals

  1. Airbnb
  2. United Kingdom
  3. England
  4. Surrey
  5. Windlesham