
Family-friendly vacation rentals in Windsor and Maidenhead
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Top-rated family-friendly rentals in Windsor and Maidenhead
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Popular amenities for Windsor and Maidenhead family-friendly rentals
Family-friendly home rentals with a hot tub

London Pad, 30 mins from Waterloo..
L'appartement de Laura est situé dans un très beau quartier de Londres, le village de Barnes comme celui de Richmond sont à découvrir ! C'est un endroit calme, à l'écart de l'effervescence de la City mais celle-ci est accessible en train (pas directement en métro, mais les trains pour la station de Waterloo sont réguliers). Nous avons passé un court séjour en famille dans ce logement et je le recommande sans hésitation pour découvrir Londres et ses environs !

Stunning 3B2Ba Huge entertaining space and hottub!
Great place and great host

London / Barnes - one bedroom flat
The flat was great for the two of us. It was comfortable, stylish and clean. There’s a nice walk through the park to barnes station for easy access into town. A positive experience overall. Laura was very helpful and easy to communicate with

The Pool House at Upper Farm (near Thame/Oxford)
We stayed in the pool house, fantastic location with a beautiful scenery. Very private and comfortable stay. Welcome book was very informative with places to visit and restaurant in area. I would advise you do a shop before, as local shops are not walking distance. We had four days of quality family time and the pool and hot tub was amazing. Highly recommended, we will be returning. Thank you Gary.
Family- and pet-friendly home rentals

Self Contained Annex
I was greeted by the host, let in to the property ,showed around and free to ask any questions. host is very friendly, and approachable. We loved to be able to use their garden (my son played there football for a bit, we looked at the chicken and horses. Host also explained easily accessible forest behind their property-perfect for a walk with our pooch before we left. Kitchen has everything you need, bed is very comfy, bathroom was good too. Will return one day again. we loved our short stay, thank you.

Garden Cottage..pretty countryside location
We stayed at Garden Cottage for a few days. The accommodation was just as described and everything was perfect for the 3 of us and the dog. The area was lovely and it was great to be able to walk to the pub and also into Bradfield. Would definitely recommend and look forward to re-visiting in the future if possible.

2 Storey Coach House Crondall, 2 KING bed, 2 bath
Perfect place to stay in lovely peaceful surroundings, lovely walks into the village with a couple of pubs, Toby and Maddy were super helpful and friendly and made us feel at home, Coach House was presented very well and exactly as described, wouldn’t hesitate to recommend.

Self contained, rural cottage, 2 double bedrooms
What a great setting for an escape to the country! I already miss waking up with the chickens and pigs to greet me every day. I also saw more wild animals and birds in my walks around here in a week, than I have in years in London. Auriol is a great host, relaxed, knowledgeable and friendly, and the property is exactly as described and shown here. Tips for other travelers: If you’re a light sleeper bring an eye mask and earplugs as it does get sunny in the main bedroom. Looking forward to returning here!

2 bed flat - SW London with parking
The flat had art deco styled decor which beautifully matched the period of the building. The host was quick to respond to requests and the access to lovely walks is fantastic. Bushy Park is a superb wilderness walk in the middle of London and goes all the way to Hampton Court Palace. I would definitely stay there again.

Mizpah Ecolodge
Lovely stay at Tim's place with my hubby Lee and our pooch Huxley. The lodge was very peaceful, warm and comfortable. And the new railway sleeper bed is fab! Tim and his co-host Paulina were good hosts, we had one small issue with the wifi, which they worked to resolve very quickly. Lovely welcome items waiting for us, which was a great touch. I work in the area quite often and wouldn't hesitate to book Tim's space again in the future.

The Old Hay Barn, Ashley Green
Very cozy, comfortable, beautiful house. Lovely walks nearby, especially for dogs. Very friendly hosts. Thoroughly recommended

Getaway Cottage Windsor
We stayed at The Clockhouse whilst visiting Windsor Castle. We would not hesitate to stop there again. Beautiful place, very peaceful. Very comfortable and nicely decorated. Fantastic stay! Thank you, Sam x
Family-friendly home rentals with a pool

The Cottage, dog friendly,swimming pool in summer
Miranda's cottage is very well situated and set up for doing as we did - enjoying the local area, taking advantage of hot summer days by the pool, and walking in the woods with kids. Highly recommended for families of 4 or even more if you're prepared to really use the space. My kids were very happy sleeping in the twin beds, and we were able to use every inch of the place.

Country House, 5bed, large garden, heated pool
Just had a fantastic Christmas break in Dan’s house. Perfect home from home, beautifully decorated for Christmas with a real tree! Thanks so much, Dan. We loved staying in your house and had a fab time.

Independent studio sleeps up to 1-4
We had a very enjoyable stay in Fiona’s residence. The property itself looks exactly like the pictures and was situated on a lovely, quiet street whilst still being situated at a nice proximity from the tube and livelier surrounding restaurants and stores. We were provided with all of the necessary amenities and we slept well on the very comfortable beds. Fiona was also a very communicative host, providing us with plenty of information about the area whilst the option for remote check-in and check-out aligned well with our schedules. Overall, we had an enjoyable stay and would come back again. Thank you!

2 bed Cottage at Sheephouse Manor
We had a great stay at Caroline's place. Her cottage is lovely and very comfortable. There were decent amenities, a nice and spacious outdoors area and the city centre is a short Uber ride away. Would recommend to anyone staying in Maidenhead.

Barn conversion, Henley-on-Thames
The barn is beautiful and very well fitted out. Fabulous setting, absolutely stunning and super peaceful and quiet. The one bathroom was challenging at times with a party of adults but the rest of the barn is faultless and such a joy to stay in. The tennis court and other amenities were fabulous.

4 Bedroom Family Home with pool
Lovely comfortable and spacious family house . Suzie the host was very friendly and obliging and made us feel very welcome in her beautiful home. Would definitely book again .

DOG FRIENDLY COTTAGE
This was a great find. The conversion has created a great space to live in, huge bedrooms, 2 super bathrroms, large kitcehn with everything in it you require, and a large living - diningroom. To use and enoy the pool ensure the suns out! Highly reccomend it and would go back for longer another time.

Stunning hideaway house
booked with miranda for a couple of nights and she couldn't have been a better host.. very helpful and responded to right awa to any queries I had.. the house and garden were both beautiful and the whole stay was very enjoyable.. would definaltet recommend 👌.
Quick stats about vacation rentals that are family-friendly in Windsor and Maidenhead
Total rentals
1.2K properties
Total number of reviews
31K reviews
Pet-friendly rentals
320 properties allow pets
Rentals with a pool
30 properties have a pool
Rentals with dedicated workspaces
490 properties have a dedicated workspace
Wifi availability
1.2K properties include access to wifi
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- British Museum
- Green Park
- Kensington Gardens
- Big Ben
- Covent Garden
- Buckingham Palace
- Trafalgar Square
- Harrods
- Barbican Centre
- Tower Bridge
- St. Paul's Cathedral
- London Bridge
- Brockwell Park
- Camden Market
- Emirates Stadium
- Wembley Stadium
- The O2
- Hampstead Heath
- ExCeL London
- London Stadium
- Alexandra Palace
- Oxford University
- Blenheim Palace
- Silverstone Circuit