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Holiday rentals in Windsor and Maidenhead

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Top-rated holiday rentals in Windsor and Maidenhead

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Top guest favourite
A cozy bedroom is depicted with a double bed featuring decorative pillows. The walls are adorned with various framed artworks and photographs, contributing to a personalized aesthetic. A small nightstand is visible beside the bed, and an open door leads to a well-lit hallway.
Guest suite in Egham
4.93 out of 5 average rating, 205 reviews

Self-contained Annex Studio Flat

The accommodation consists of a double bedroom with French doors opening onto a nice big garden. There is a fully fitted kitchen and a small bathroom with walk-in shower. Broadband, TV, fridge, washing machine and drier are all included. It is about 50 yards from Egham station which has regular trains to London, the journey taking about 40 minutes. The train goes to Waterloo Station which is very close to the London Eye and Westminster, with Buckingham Palace, St James Park, Trafalgar Square a short walk away. Heathrow Airport is 5 or 6 miles away. Egham is a small town, but it has some historic interest in that the Magna Carta was signed at Runnymede down the road by the river in 1215. Not far away is Windsor castle and Eton (where princes William and Harry, and David Cameron went to school). There is also some lovely countryside around and lovely walks.

Guest favourite
The exterior of the Coach House displays a combination of traditional brickwork and modern design. Black doors are framed by large windows, while a small stone table with chairs is positioned by the entrance. Decorative plants add a touch of greenery to the inviting facade.
Home in Windsor and Maidenhead
4.95 out of 5 average rating, 259 reviews

Historic building in the centre of Windsor.

Beautifully renovated 1850's Coach House. This is part of a building that housed Queen Victoria's Equerries at Windsor Castle. Based in central Windsor with private parking, the property is an ideal place for a staycation. Mess about on the river (boating, paddle boarding, swimming) or visit the many beauty spots in the area. Legoland, Windsor Great Park, Windsor Castle and Swinley mountain bike trails are all within easy reach. A unique property that we hope that you will love as much as us.

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 Warfield
4.91 out of 5 average rating, 835 reviews

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. Breakfast is not provided. 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

Guest favourite
A bright living area features two large sofas in green tones and a stylish glass coffee table. A dining table with four chairs is set for a meal, complemented by wall art and natural light from a window with curtains.
Flat in Berkshire
4.95 out of 5 average rating, 169 reviews

Apartment in Windsor

Newly refurbished apartment located 10 minutes walk from Windsor Castle and the town centre with all of its great shops, bars, restaurants and tourist attractions. Benefits from its own private entrance, double bedroom, wet room, kitchen and separate living room with 2 large sofas and dining area. Easy access to the M4 and only a 10 minute walk to the train station with direct links into London, it is ideally located for a business stay or as a base to explore Windsor and the surrounding area.

Top guest favourite
The entrance to the Garden View Suite is framed by vibrant flower boxes on either side. A clear glass door, with a welcoming sign, invites guests into the private space. A small gate leads to a lush garden area filled with greenery.
Guest suite in Old Windsor
4.97 out of 5 average rating, 296 reviews

Garden View Annex Private Free parking River walks

Take a gentle walk from here along the Thames Path to historic National Trust Runnymede, with its tea shop, many monuments to Magna Carta and beautiful outdoor art works. Less than 2 miles from The Long Walk, explore Windsor and the Castle or visit Saville Garden in the Great Park. We're also close to Legoland. Old Windsor has lots of places to eat (see guidebook) all in walking distance, we're surrounded by beautiful walks and we're also on the direct bus route to Windsor and Heathrow.

Guest favourite
A cozy sleeping area features a spacious bed with neutral bedding against a softly colored wall. A small armchair and a light-colored rug complement the wooden flooring. Wall-mounted shelves display framed images, and a small closet provides additional storage.
Guest suite in White Waltham
4.94 out of 5 average rating, 435 reviews

Completely separate self-contained studio flat

Self-contained double room with en-suite shower room and kitchen area. Private access and parking. Completely private stand-alone studio but part of our home. Suitable for professional person/couple for short let periods. Ideal Monday-Friday but good for weekends to visit local area too. Free wi-fi, TV. A car is essential. Located in White Waltham village just outside Maidenhead. Easy access to Junction 8/9 of M4 and Maidenhead station. Also handy for Windsor, Henley, Ascot, Reading

Guest favourite
The exterior of the Grade 11 listed Mews property is shown, featuring a combination of brick and tile. A spacious courtyard is visible, bordered by trees and carefully arranged pathways. Private gates provide security, while the surrounding landscape includes greenery and open sky.
Home in Englefield Green
4.93 out of 5 average rating, 111 reviews

5* Boutique House Nr Windsor Castle, Ascot, London

This Grade 11 listed Mews property was built in 1872 and offers contemporary, five star living space. Luxurious king size beds, beautiful bathrooms, abundant art and character; the property 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 within 6 miles. Central London is 35 minutes by train. Heathrow is 6 miles away.

Top guest favourite
A cozy studio space is showcased, featuring a king-size bed with light bedding and decorative pillows. Natural light enters through large windows, illuminating the comfortable seating area with a patterned rug. A small bookshelf adorns the wall, adding a touch of warmth to the inviting atmosphere.
Flat in Datchet
4.98 out of 5 average rating, 217 reviews

Stylish Studio-Walk to Windsor/Eton/Thames/Parking

Welcome to Crail Cottage in Datchet. Surrounded by beautiful greenery, there is plenty of wildlife and the River Thames is just behind the house. Take a walk to Windsor and Eton via the home park or the riverside. You can even walk to Eton through the school grounds from here. Our little studio is freshly decorated and welcomes you to stay. There is a new addition which is a King size bed with Hypnos mattress that will guarantee you a good night sleep. Perfect to relax after a busy day.

Top guest favourite
A brick pathway leads to the front entrance of a Victorian house, framed by a wrought-iron fence. The exterior features a combination of stone and brick, with decorative detailing. Lush greenery and flowering plants provide color along the pathway and around the property.
Guest suite in Reading
4.95 out of 5 average rating, 190 reviews

Private double bedroom and en-suite bathroom

We are located very near the Royal Berkshire Hospital and University of Reading. We have a bedroom, garden room and bathroom for people to use during their stay (nothing is shared). There is a separate entrance to the guest's accommodation and there is no access to the main house. We have a cat who sleeps in the adjoining room (our utility room), but will not have access when guests stay. There is no breakfast supplied. There is on road parking on weekday evenings and weekends.

Top guest favourite
The entrance to the house features a covered porch framed by lush greenery and climbing plants. A pathway leads to the front door, which opens into a welcoming lobby. Stacked logs are visible beside the entrance, adding a rustic touch to the outdoor space.
Apartment in Berkshire
4.97 out of 5 average rating, 190 reviews

Cheerful modern apt central Maidenhead, parking

Quiet location with free driveway parking, excellent road/rail links to London. On a tree lined street, 7 minutes walk from the Town Centre and Railway Station (London or Oxford 1hr max) The private space includes 2 double bedrooms, a large bathroom, en-suite shower room, a well equipped kitchenette and a relaxing lounge area Maidenhead Town Centre is being transformed with new restaurants, bars, coffee shops, and a new Leisure Centre 20 mins walk

Top guest favourite
A charming wooden barn is set amidst lush greenery and tall trees. A tranquil pond with water lilies reflects the surrounding foliage. Bright sunlight illuminates the scene, enhancing the peaceful outdoor space and the rustic charm of the barn.
Guest house in Buckinghamshire
4.98 out of 5 average rating, 257 reviews

The Barn at The Grove

The Barn is a self-contained recently converted space in the heart of the Chilterns. It is close to the riverside towns of Henley-on-Thames and Marlow and the surrounding Chiltern countryside. It is located on the edge of the village of Frieth with nearby farm shops and local gastro-pubs within a 5 min drive. The Barn is in a private and peaceful location with off-street parking. It is perfect for couples, solo travellers and small families.

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 Windsor and Maidenhead
4.96 out of 5 average rating, 810 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.

Popular amenities for Windsor and Maidenhead holiday rentals

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Avg. price$170 SGD$164 SGD$167 SGD$183 SGD$195 SGD$217 SGD$208 SGD$201 SGD$192 SGD$187 SGD$180 SGD$188 SGD
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Quick stats about holiday rentals in Windsor and Maidenhead

  • Total holiday rentals

    Explore 2,520 holiday rentals in Windsor and Maidenhead

  • Verified guest reviews

    Over 78,250 verified reviews to help you choose

  • Family-friendly holiday rentals

    1,220 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 530 rentals that welcome pets

  • Holiday rentals with a pool

    60 properties feature pools

  • Rentals with dedicated workspaces

    1,020 properties have a dedicated workspace

  • Wifi availability

    2,430 of Windsor and Maidenhead holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Windsor and Maidenhead rentals

  • 4.7 Average rating

    Windsor and Maidenhead stays receive an average rating of 4.7 out of 5 from guests

  • Nearby attractions

    Windsor and Maidenhead’s top spots include Ascot Racecourse, Virginia Water Lake and Odeon Maidenhead

Destinations to explore