
Family-friendly holiday rentals in Maidenhead
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Top-rated family-friendly rentals in Maidenhead
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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

The Studio in Maidenhead Riverside, Berkshire, UK.
LARGE STUDIO: (T0) A large self-contained quiet studio with UK size 2m double bed, en-suite bathroom and kitchenette with it's own private entrance. Attached to our house. There is off-street parking for 1 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.

Charming terrace in the heart of Bray village
Our lovely victorian terraced home is perfectly situated for all the fine dining that the charming village of Bray has to offer. The Michelin 3-starred Waterside Inn and Fat Duck are a few mins walk away as are the Crown Inn, Hinds Head and Caldesi. Stroll 15 mins more and you’ll find the recently renovated Monkey Island Estate. A short drive and you can be at either Ascot or Windsor Races, Cliveden House, Legoland, the village of Cookham or the beautiful river Thames towns of Marlow or Henley

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.

A Hidden Gem
A character cottage, tucked away, in the heart of gastronomic Bray - renowned for its Michelin-starred restaurants: The Waterside, The Fat Duck, the Hind's Head and Caldesi, all within easy walking distance of the cottage. Lych Cottage is a two-bed semi-detached property, completed to a high standard. It provides a stylish place to stay for those wishing to enjoy the comforts of home whilst availing themselves of the local amenities. The first night's stay includes a continental breakfast.

Charming Cottage, dogs welcome, private garden .
A pretty cottage fully equipped for a comfortable holiday/ stay! Set back from the road, a peaceful haven. Private garden & parking. Easy walk to all local amenities & The River Thames. Great pubs &Michelin Star restaurants locally. The Chiltern Way offers a stunning path to all cyclists & walkers. Gorgeous old Towns of Windsor ( Legoland& Castle) Henley( Regatta & Festival)& Marlow (Tom Kerridge) , Cliveden, The Stanley Spencer Gallery,Train -London Paddington. M4 M40, Bicester Village .

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

Smart Loft annex in Cookham
Lovely first-floor loft annex on a quiet lane, just a few minutes’ walk from Cookham’s centre and its historic High Street with 7 pubs and restaurants. Bright and airy, the property is ideal for those seeking a village retreat: couples, small families, and business travellers. It features a double bedroom, lounge area with sofa bed (sleeps 1 adult), and separate bathroom. It has its own entrance and parking space within a secluded gated property. SkyTV with Sky Cinema/Kids/Sky/BT Sports.

Studio West & Petting Farm-Near Legoland- Lapland
STUDIO WEST is located at Willow Court Farm in Oakley Green and only 5-10 minutes drive away from LEGOLAND, Lapland UK and Windsor town centre so is perfectly located for a great stay. We have private award winning detached open plan modern holiday studios providing unique accommodation with easy access to the all the fantastic places to visit in the surrounding area. Guests can feed the various animals on the farm including the 6 pigs, 9 pygmy goats, 6 sheep, turkey ducks and chicken.

Southwood Gardens annexe in Cookham
We are right on the edge of the beautiful village of Cookham. The accommodation is annexed to the main house and is accessed through a secured side-gate for total privacy. There is also free private parking on the front drive. The room is ideal for people who need to commute (1 hour by train to London, 25 minutes drive to Heathrow), or families who need to have additional accommodation for their loved ones to stay in the area. We very much look forward to welcoming you to Cookham soon !

Stunning Place near Windsor & Heathrow, 3BR House
A stunning, spacious 3-bedroom home, perfect for families! Just a short walk to shops and parks, and short drive from Burnham Station, Heathrow, and Windsor Castle. This gorgeous, newly refurbished house features contemporary decor, new flooring, and furniture. It’s an adorable space with free parking, WiFi, a 4K Ultra Smart TV, and a serene village atmosphere. Enjoy the peaceful, "home away from home" feel, perfect for relaxing after a day of exploring. Book now for a cozy, modern stay!

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
Popular amenities for Maidenhead family-friendly rentals
Family-friendly home rentals with a hot tub

Racecourse Marina Lodge | Hot tub | Parking | EV

Tinkerbell Retreat

Luxury self-contained Annexe with balcony Jacuzzi

Luxury Lakeside Hut | Hot Tub | Near Harry Potter

Riverside Log Cabin+Luxury Hot Tub Spa+Copper bath

Luxury Glamping Retreat near London

Tree House - Hot Tub on balcony

Luxury rural thatched cottage with cedar hot tub.
Family- and pet-friendly home rentals

Shal Inn@ Heathrow -pick & Drop + free Parking

Gardener's Bothy loft apartment, peaceful location

Marlow F3 A Lovely 1-bed apartment- WiFi & Parking

The Garden Cabin

Luxury Shepherd's Hut with stunning sunset views!

Elegant Central Henley Apartment

Gorgeous CountryCottage overlooking Windsor Castle

Self contained Barn, Idyllic location, Binfield
Family-friendly home rentals with a pool

The Mill House

Henley apartment with heated pool

Luxury retreat with extensive leisure facilities

Spacious Sunny Apartment

Family friendly - rural, detached, home from home

The Coach House

Two Bed Large Countryside Barn with Indoor Pool

Romantic hot tub, and private heated pool retreat.
Quick stats about holiday rentals that are family-friendly in Maidenhead

Total holiday rentals
Explore 120 holiday rentals in Maidenhead

Nightly prices starting at
Maidenhead holiday rentals start at $64 SGD per night before taxes and fees

Verified guest reviews
Over 2,290 verified reviews to help you choose

Pet-friendly holiday rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
120 of Maidenhead holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Maidenhead rentals

4.7 Average rating
Maidenhead stays receive an average rating of 4.7 out of 5 from guests
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- Family-friendly rentals Berkshire
- Family-friendly rentals England
- Family-friendly rentals United Kingdom
- Tower Bridge
- Big Ben
- Paddington
- British Museum
- Covent Garden
- Natural History Museum
- London Bridge
- Marble Arch
- Buckingham Palace
- Tottenham Court Road
- Hampstead Heath
- St Pancras International
- Kings Cross
- The O2
- Trafalgar Square
- Piccadilly Theatre
- Wembley Stadium
- Battersea Power Station (disused)
- ExCeL London
- Emirates Stadium
- Royal Albert Hall
- Olympia Events
- Russell Square
- Borough Market




