Family-friendly vacation rentals in Windsor and Maidenhead

Spacious & light 2bd, 2ba in the heart of Windsor

This beautiful 2bed, 2bath apartment, with parking, in the heart of Windsor, is an exceptional find. With Windsor Castle (watch the marching bands for the Changing of the Guard pass right outside your front door!), Windsor Great Park, The Guildhall, beautiful Eton and its own historic town centre with fabulous shops, restaurants, bars and clubs all only minutes away on foot, you couldn't be better placed for your stay. Windsor is also a very short drive from both Ascot Racecourse and Legoland.

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.

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

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.

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.

Luxury ♥️ 1 bed apartment Windsor Legoland Heathrow

Private self contained bungalow situated close to Windsor town centre. One-bedroom boutique style property plus a double pullout sofa bed, equipped with fully-fitted kitchen , lounge and bathroom with washing machine. Ideal for families visiting Legoland or historic Windsor, with excellent transport links, travel to central London takes just under an hour from Datchet station. Luxury features including a 'rain' shower, 400 thread count Egyptian cotton bedsheets Dolce gusto coffee machine

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

Self-contained studio Wokingham

A self-contained newly build 20 m2 studio with separate entrance and parking. The studio is comprised of an en-suite bathroom, a super-king bed, a tall boy and a work desk. A kitchenette just next to the room with fridge freezer, microwave, kettle, toaster, coffee machine, washing machine and a tumble dryer. “The kitchenette doesn’t have a stove or an oven.” The studio is brand new and built to high standards. The studio is a 15 minutes walk to Wokingham train station and town centre.

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.

Saddlers Rest perfect for LaplandUK & Legoland

A cosy 1860s Victorian cottage located opposite Windsor Racecourse. Just under a 3-5 minute drive to Windsor Castle and 8-10 minutes to Legoland, with an easy train ride to London via the Elizabeth Line. Lapland UK is only 20 minutes away by car. Ideal for families visiting Legoland and Windsor Castle, couples looking for a getaway, or friends seeking a relaxing time. Perfect for race days or events at Windsor Racecourse, with Dorney Lake just 10-15 minutes away.

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

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.