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Kid-friendly vacation rentals in Windsor and Maidenhead

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Top-rated kid-friendly rentals in Windsor and Maidenhead

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

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Cottage in Windsor and Maidenhead

4.78 out of 5 average rating, 123 reviews

Enchanting, Stylish Country Garden Cottage

A convenient escape to the country; popular for focused work trips, convenient mini breaks, family holidays or longer term lets. Our self contained countryside cottage offers a calm, stylish space. Tastefully decorated to an high standard. Sleeps up to 5 people. 2 double beds & 1 single. Well equipped kitchen & dining area. Outside space & garden area. Super rural walks but only 35 minutes by train to London. River Thames nearby. Pets welcome. "Stunningly peaceful, wake to bird song each day"

Home in Windsor and Maidenhead

4.96 out of 5 average rating, 215 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.

Rental unit in Windsor and Maidenhead

4.97 out of 5 average rating, 224 reviews

The Studio in Maidenhead Riverside, Berkshire, UK.

LARGE STUDIO: (T0) This is a large self-contained quiet studio with King size bed, en-suite bathroom and kitchenette with it's own private entrance. Attached to our house. There is off-street parking for one guest car. Convenient for the A4, M4, M40 M25 London is 25 miles. Heathrow Airport is 15 minutes away by car.. Direct trains into London. The Elizabeth Line train runs from Maidenhead station direct to London and the West End. Good for Windsor, Ascot, River Thames, Pinewood Studios etc.

Guesthouse in Binfield

4.99 out of 5 average rating, 138 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 suite in Old Windsor

4.97 out of 5 average rating, 229 reviews

Self Contained Garden View Suite, Old Windsor.

Ideal for exploring historic Runnymede with its monuments and outdoor art works, and for walks along the Thames Path. Close to Windsor Great Park, Windsor Castle and Legoland. Nearest entrances into Windsor Great Park are Bears Rail for the Long Walk (walkers only because it enters the deer enclosure) & Bishopsgate for The Savill Garden. Old Windsor has plenty of places to eat (see guidebook) all within walking distance, or visit Windsor town centre for shops, the castle and Legoland.

Guest suite in White Waltham

4.94 out of 5 average rating, 381 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

Rental unit in Datchet

4.99 out of 5 average rating, 135 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.

Rental unit in Buckinghamshire

4.91 out of 5 average rating, 115 reviews

Wisteria, barn conversion in stunning location

One of three self-contained apartments created from the old barn. The location is unique! Just a short walk to the Thames tow path and close to the breath-taking Dorney Rowing Lake. The barn overlooks fields in all directions and is the last building in Dorney, occupying a uniquely peaceful location. The M4 is within a 10 minute drive, the attractions of Windsor such as Legoland are easily reached. If you are looking for a base whilst working in Slough, we are just a short drive away.

Cottage in Englefield Green

5 out of 5 average rating, 314 reviews

2 Bedroom Luxury Cottage (Secure & Quiet)

This charming Cottage is located in the picturesque Village of Englefield Green. Just four miles from Windsor Castle, three miles from Wentworth Golf Course and six miles from Ascot Race Course. Heathrow Airport if just six miles away. 300 metres further down the lane is The Royal Air Force Memorial and below that, on National Trust grounds that skirts the River Thames is the Magna Carta Memorial. The Royal Holloway University is a ten minute stroll across the Village.

Condo in Berkshire

4.94 out of 5 average rating, 140 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

Cottage in Windsor and Maidenhead

4.97 out of 5 average rating, 735 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.

Rental unit in Windsor and Maidenhead

4.95 out of 5 average rating, 322 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.

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Popular amenities for Windsor and Maidenhead kid-friendly rentals

Free parking on premises

Air conditioning

Kid-friendly house rentals

Home in Surrey

4.92 out of 5 average rating, 142 reviews

House Sleeps 5, 2 min walk to Train station.

Home in Englefield Green

4.88 out of 5 average rating, 160 reviews

Charming 5* Hse Near Windsor Castle, Ascot, London

Home in Surrey

4.85 out of 5 average rating, 149 reviews

The Orchard

Home in Seer Green

4.81 out of 5 average rating, 139 reviews

Modern Eco-Annex set within Meadow

Home in Wooburn Green

4.89 out of 5 average rating, 141 reviews

18th century cottage

Home in Bracknell Forest

4.93 out of 5 average rating, 193 reviews

2 bed house, close to Town Centre

Home in Wraysbury

4.97 out of 5 average rating, 105 reviews

River Thames near Windsor, Heathrow & London

Home in Old Windsor

4.96 out of 5 average rating, 195 reviews

Getaway Cottage Windsor

Kid-friendly apartment rentals

Rental unit in Colnbrook

4.9 out of 5 average rating, 132 reviews

Modern apartment close to Heathrow/Windsor/slough

Rental unit in Buckinghamshire

4.94 out of 5 average rating, 101 reviews

One bedroom flat in Marlow

Rental unit in Windsor and Maidenhead

4.86 out of 5 average rating, 126 reviews

2 Bedroom Flat, walking distance to town centre

Rental unit in Oxfordshire

4.96 out of 5 average rating, 167 reviews

Self contained studio flat in Henley on Thames

Rental unit in Bourne End

4.95 out of 5 average rating, 154 reviews

Cosy Studio Flat on Rural Thames

Rental unit in Slough

4.82 out of 5 average rating, 239 reviews

Lovely Slough Home Near Heathrow & Windsor

Rental unit in Windsor and Maidenhead

4.82 out of 5 average rating, 152 reviews

Hampden Apartments - The Edward

Rental unit in Oxfordshire

4.98 out of 5 average rating, 180 reviews

Cosy annexe by shops/parking, 15min walk to Henley

Kid-friendly condo rentals

Condo in Reading

4.92 out of 5 average rating, 212 reviews

Smart studio incl. breakfast. Easy access to town

Condo in Surrey

4.81 out of 5 average rating, 105 reviews

Lovely 1 bed flat

Condo in Arborfield

4.94 out of 5 average rating, 156 reviews

2 bedroom flat in beautiful oak framed building

Condo in Windsor

4.92 out of 5 average rating, 118 reviews

Windsor Best location! luxury 2Bed 2Bath +Garden

Condo in Oxfordshire

4.99 out of 5 average rating, 166 reviews

Beautiful Henley apartment w/ secure gated parking

Condo in Windsor and Maidenhead

4.84 out of 5 average rating, 101 reviews

Central Windsor, free parking,2 bedroom apartment

Condo in Harrow on the Hill

4.93 out of 5 average rating, 109 reviews

Stylish newly decorated one bedroom flat.

Condo in Marlow

4.98 out of 5 average rating, 202 reviews

Central Marlow modern apartment close to High St.

Quick stats about vacation rentals that are kid-friendly in Windsor and Maidenhead

Total rentals
270 properties
Total number of reviews
13K reviews
Family-friendly rentals
190 properties are a good fit for families
Pet-friendly rentals
70 properties allow pets
Rentals with a pool
20 properties have a pool
Rentals with dedicated workspaces
170 properties have a dedicated workspace

Destinations to explore