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Family-friendly vacation rentals in Windsor and Maidenhead

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Windsor and Maidenhead family-friendly rentals

Family-friendly home rentals with a hot tub

Loft in London
4.71 out of 5 average rating, 75 reviews

London Pad, 30 mins from Waterloo..

MarlèneRating, 5 stars8 months ago
Laura's apartment is located in a very beautiful area of London, the village of Barnes and Richmond are to be discovered! It's quiet, away from the hustle and bustle of the City but it's accessible by train (not directly by subway, but trains to Waterloo station are regular). We had a short stay with the family at this place and I would definitely recommend it to discover London and its surroundings!
Condo in Raynes Park
4.78 out of 5 average rating, 9 reviews

Stunning 3B2Ba Huge entertaining space and hottub!

BrunaRating, 5 stars4 months ago
Great place and great host
Apartment in London
4.95 out of 5 average rating, 38 reviews

London / Barnes - one bedroom flat

Clare Rating, 5 stars9 months ago
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
Guest favorite
Farm stay in Chinnor
4.92 out of 5 average rating, 133 reviews

The Pool House at Upper Farm (near Thame/Oxford)

JulieRating, 5 stars1 week ago
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

Top guest favorite
Apartment in Pamber Green
4.92 out of 5 average rating, 142 reviews

Self Contained Annex

LindaRating, 5 stars2 weeks ago
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.
Guest favorite
Bungalow in Tutts Clump
4.96 out of 5 average rating, 289 reviews

Garden Cottage..pretty countryside location

JonathanRating, 5 stars1 week ago
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.
Superhost
Home in Crondall
4.85 out of 5 average rating, 120 reviews

2 Storey Coach House Crondall, 2 KING bed, 2 bath

AlanRating, 5 stars1 week ago
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.
Guest favorite
Cottage in Ibworth
4.94 out of 5 average rating, 172 reviews

Self contained, rural cottage, 2 double bedrooms

DeeRating, 5 stars1 week ago
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!
Superhost
Apartment in Hampton Wick
4.78 out of 5 average rating, 141 reviews

2 bed flat - SW London with parking

ElizabethRating, 5 stars5 months ago
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.
Guest favorite
Chalet in Benson
4.91 out of 5 average rating, 279 reviews

Mizpah Ecolodge

LouiseRating, 5 stars1 month ago
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.
Superhost
Guesthouse in Buckinghamshire
4.89 out of 5 average rating, 149 reviews

The Old Hay Barn, Ashley Green

GavinRating, 5 stars1 month ago
Very cozy, comfortable, beautiful house. Lovely walks nearby, especially for dogs. Very friendly hosts. Thoroughly recommended
Top guest favorite
Home in Old Windsor
4.97 out of 5 average rating, 211 reviews

Getaway Cottage Windsor

SarahRating, 5 stars2 weeks ago
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

Superhost
Cottage in Wolverton Common
4.87 out of 5 average rating, 47 reviews

The Cottage, dog friendly,swimming pool in summer

OliverRating, 5 stars33 months ago
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.
Home in Cookham
5 out of 5 average rating, 34 reviews

Country House, 5bed, large garden, heated pool

DamionRating, 5 stars4 months ago
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.
Guesthouse in Ealing
4.83 out of 5 average rating, 23 reviews

Independent studio sleeps up to 1-4

PhoebeRating, 5 stars22 months ago
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!
Apartment in Maidenhead
4.8 out of 5 average rating, 5 reviews

2 bed Cottage at Sheephouse Manor

JamesRating, 5 stars77 months ago
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.
Superhost
Home in Oxfordshire
4.87 out of 5 average rating, 224 reviews

Barn conversion, Henley-on-Thames

JuliaRating, 5 stars6 months ago
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.
Home in Wargrave
4.88 out of 5 average rating, 8 reviews

4 Bedroom Family Home with pool

LukeRating, 5 stars83 months ago
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 .
Superhost
Guesthouse in Tadley
4.75 out of 5 average rating, 25 reviews

DOG FRIENDLY COTTAGE

Ros & LizRating, 5 stars47 months ago
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.
Superhost
Home in Tadley
4.78 out of 5 average rating, 23 reviews

Stunning hideaway house

AidanRating, 5 stars22 months ago
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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