Kid-friendly holiday rentals in Windsor and Maidenhead

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Top-rated family-friendly rentals in Windsor and Maidenhead

Guests agree: these family-friendly rentals are highly rated for location, cleanliness and more.

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Guest favourite

Apartment in Berkshire

4.97 out of 5 average rating, 103 reviews

Cheerful modern apt central location, 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 a double bedroom, a large bathroom, a second bedroom with a double sofa bed and en-suite shower room, a well equipped kitchenette and a cosy sitting room Maidenhead Town Centre is being transformed with new restaurants, bars, coffee shops, and a super new Leisure Centre 20mins walk

Guest favourite

Guest house in Datchet

4.94 out of 5 average rating, 388 reviews

Luxury ♥️ 1 bed apartment Windsor Legoland Heathrow

Brand new, self contained bungalow situated close to Windsor town centre. One-bedroom boutique style property, with 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

Guest favourite

Barn in Warfield

4.91 out of 5 average rating, 736 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. A few miles from Ascot and Royal Windsor, Train stations to London and Reading.

Superhost

Guest suite in Maidenhead

4.83 out of 5 average rating, 696 reviews

Oak Barn - 1st Floor self contained Studio

Light and spacious apartment in a stand-alone annexe in the grounds of our house, 250m from the River Thames. Modern furniture, TV, wifi, full kitchen, washing machine, freezer. Great location for eating out and for access to countryside. Close to Windsor, Eton, Marlow, Cliveden National Trust and lovely river walks. 5 minutes from Maidenhead station. 10 minutes from The Fat Duck and the Waterside Inn. We are near a railway line. It doesn't bother us at all but you can hear the trains.

Guest favourite

Guest house in Binfield

4.98 out of 5 average rating, 113 reviews

The Brickmaker’s Loft

A newly fitted one bedroom apartment, with living area, full kitchen, large bedroom with king size bed, a full size single bed in the eaves, and an extra single bed if needed. We’ve kitted the Brickmaker’s Loft out with everything you would need. The kitchen has an oven, fridge, dishwasher, kettle, toaster, microwave and all the normal cooking bits, crockery etc. The bathroom has a walk-in shower, loo, and sink, and a washing machine if you need it. The bedroom is a lovely relaxing space.

Guest favourite

Guest suite in White Waltham

4.95 out of 5 average rating, 347 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

Cabin in Windsor

4.97 out of 5 average rating, 232 reviews

Cabin With Private Garden Near Legoland & Castle

Cosy Self-Contained Cabin with It’s own private garden space & separate entrance. Free on-street parking. Only 15-20 minutes walk to Windsor Town Centre, Bars, Restaurants, Windsor Castle & Train Stations. Perfectly located for visitors to Legoland, Lapland and Ascot Races. Close to lovely walks & cycling along Thames Path & Windsor Great Park. Near Heathrow. The Cabin sleeps 2-4 guests. Double Bed & Sofa Bed. Lounge/Dining Area, Kitchenette, Bedroom & Shower Room/Macerator WC.

Guest favourite

Apartment in Buckinghamshire

4.94 out of 5 average rating, 144 reviews

Gardener's Bothy loft apartment, peaceful location

Loft apartment, Gardeners Bothy, completely newly refurbished, in converted barn in unique rural location. Minutes walk from the Thames towpath and Dorney Rowing lake. 10 minutes drive to the M4, close to Windsor town centre and handy for Slough Trading Estate, difficult to believe this is all so close to this unique and peaceful location overlooking fields and Dorney Common. Lovely place for walkers and great base for many local attractions. Ideal spot to work or just relax.

Guest favourite

Cabin in Old Windsor

4.94 out of 5 average rating, 123 reviews

Gorgeous Self-Contained Wooden Cabin - Old Windsor

Beautiful and spacious self-contained log cabin with 1 king size bed & 1 folding double bed. Shower/toilet, lounge and kitchenette. Work Station Close to Heathrow (7.4 miles / 15 mins) Great access to Windsor (2.4 miles). Close to a bus stop if needed. 2.5 miles to Runneymede where the Magna Carta was signed. Easy access to Ascot and Legoland The cabin is in the owner's garden. A dog (Labrador) lives on site, so please only book if comfortable around dogs.

Guest favourite

Cottage in Windsor and Maidenhead

4.97 out of 5 average rating, 690 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.

Guest favourite

Flat in Windsor and Maidenhead

4.95 out of 5 average rating, 268 reviews

Windsor Great * Snug * Private Annexe with Parking

*stylish private annexe with off street parking for one car. * self contained studio attached to our family home. * suitable for up to 2 people only. * ideal for both work travellers (key box ) and tourists. * approx 21 m2 *quiet, leafy "Boltons" area. * 15\20 mins stroll to town centre and Castle. * 10 mins stroll to Long Walk and Great Park. * 5 mins cycle to Windsor Great Park cycle path. * local shop and pub 5-10 mins walk.

Guest favourite

Home in Berkshire

4.95 out of 5 average rating, 101 reviews

Robin’s Rest @ Scotlands House

Enjoy peaceful views of robins and deer across a field towards a stream. This unique space is peaceful and tranquil yet is also walking distance from the hustle and bustle of The Lexicon in Bracknell. Finished to an exceptional standard, Robin’s Rest @ Scotlands House offers luxury and tranquility, ideal for a weekend escape or longer stay.