
Family-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 homes are highly rated for location, cleanliness and more.

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.

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

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.

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.

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.

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

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

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.

Budget Bliss in High Wycombe
A unit on its own, away from the main residence, this is a modern, comfortable annexe with a high-end finish. Ideal for people working in the area, short stops or longer stays. Even for those looking for long country walks and a home away from home for some peace and quiet downtime. Ensuite with a double bed, kitchenette with 2 burner hob, fridge freezer, microwave and lots of storage with a separate built in wardrobe. Sleeps 2 comfortably.

Literary Annexe by the Long Walk
A town centre location in Windsor's residential "Golden Triangle". One minute from the famous Long Walk, this is a private annexe- part of a grade two listed house in a unique cul-de-sac. Two charming bedrooms and a cosy living area with book lined shelves, TV and a sunny aspect. There is free parking for one car.
Popular amenities for Windsor and Maidenhead family-friendly rentals
Family-friendly home rentals with a hot tub

The Pool House

Oak Tree Retreat

The Woodland Cabin with Private Hot Tub Spa

Tinkerbell Retreat

Christmas Barn, private heated pool and hot tub

Luxury self-contained Annexe with balcony Jacuzzi

Luxury Woodland Hideaway with Private Hot Tub

Riverside Log Cabin+Luxury Hot Tub Spa+Copper bath
Family- and pet-friendly home rentals

Stylish 2 bedroom flat; parking included

Gorgeous CountryCottage overlooking Windsor Castle

Windsor -Castle 5 min walk lux 2 Bed 2bath+Garden

Self contained Barn, Idyllic location, Binfield

Charming Cottage, dogs welcome, private garden .

2 bed house, close to Town Centre

Private Annex En suite Double Room (Dog Friendly)

Spacious 3 bedroom family home, with parking.
Family-friendly home rentals with a pool

Luxury Battersea studio w open fire, close to Park

Family friendly - rural, detached, home from home

Bell Tent Glamping Single unit, self contained.

The Coach House

Stunning 1 Bed in Battersea w/ Pool, Gym & Rooftop

Delightful Cottage 15 Acre Estate + Pool + Hottub

Unique 1-bd penthouse 3 minutes walk to Excel/o2

Escape to Country Living at its Finest!
When is the best time to visit Windsor and Maidenhead?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $260 AUD | $264 AUD | $275 AUD | $306 AUD | $326 AUD | $381 AUD | $384 AUD | $361 AUD | $336 AUD | $310 AUD | $294 AUD | $300 AUD |
| Avg. temp | 6°C | 6°C | 8°C | 11°C | 14°C | 17°C | 19°C | 19°C | 16°C | 12°C | 8°C | 6°C |
Quick stats about holiday rentals that are family-friendly in Windsor and Maidenhead

Total holiday rentals
Explore 1,220 holiday rentals in Windsor and Maidenhead

Verified guest reviews
Over 33,710 verified reviews to help you choose

Pet-friendly accommodation
Find 350 rentals that welcome pets

Holiday rentals with a pool
40 properties feature pools

Rentals with dedicated workspaces
510 properties have a dedicated workspace

Wi-Fi availability
1,190 of Windsor and Maidenhead holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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
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- Family-friendly rentals Berkshire
- Family-friendly rentals England
- Family-friendly rentals United Kingdom
- Tower Bridge
- British Museum
- Westminster Abbey
- Big Ben
- London Bridge
- Covent Garden
- Buckingham Palace
- Trafalgar Square
- The O2
- Hampstead Heath
- Wembley Stadium
- St. Paul's Cathedral
- St Pancras International
- Emirates Stadium
- ExCeL London
- Camden Market
- London Stadium
- Clapham Common
- Alexandra Palace
- Goodwood Motor Circuit
- Oxford University
- Blenheim Palace
- Primrose Hill
- Queen Elizabeth Olympic Park, London




