
House holiday rentals in Windsor and Maidenhead
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Top-rated house rentals in Windsor and Maidenhead
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Popular amenities for Windsor and Maidenhead house rentals
House rentals with a pool

The Mill House
We stayed at the house for weekend of birthday celebrations, the house was great and the garden, pool and surroundings were fabulous. The kitchen area was perfect for gatherings and loads of space to unpack. The beds were really comfortable, maybe an option to have a couple of additional twin beds as the majority were all double. The house was spotless and with the weather being perfect we couldn’t have asked for more. Anne was accommodating in all requests and information about the local area. I would highly recommend this property, we had a fabulous weekend.

Spacious & stylish family home
Ann’s house was exactly what we were looking for and we had a wonderful stay and felt very much at home. Everything was easy to find and use and the house had all the amenities we needed for a family of 5. The neighborhood was lovely and we loved walking around.

Berkshire country house with pool
We spent Christmas at Salix House and we were 11 pax in the party. Charlotte is an amazing hostess and her property is absolutely fabulous! The house is very well equipped and there’s so much to do: ping pong table, football, books and bars games. We had a fantastic time there and we would love to book to go in the summer! Thank you so much Charlotte

Bright spacious home with natural swimming pond
This is an amazing and beautiful eco property. Ivana and John have spent a lot of time carefully considering so many aspects of their beautiful home. The location is so peaceful. The beautiful aspect across their garden meant you could see wildlife and bunnies and beautiful sunrises. 🌅 All beds were super comfy. The wood burner was cozy. The sofa was great for a family and their TV stereo set up was brilliant. There are ALOT of lights etched to get used to, that create mood lighting in each room and Ivana manages the heating of the property remotely.

Pool & Piano | Hidden Oasis in Kensington Olympia
very nice and cooperative host. lovely place.

Barn conversion, Henley-on-Thames
A beautiful barn conversion in lovely grounds with lots of facilities, with thoughtful and helpful hosts. It was a fabulous long weekend and we didn’t need to leave the grounds to be entertained throughout, from in the pool to playing pool, it was all we could ask for.

The Place: 2-Bedroom Getaway
Our stay was exceptionally great. The train station is close which made our movements easy. The place was very clean. There was easy access to food and groceries. Chioma was very helpful and accommodating. We were able to check in earlier than the scheduled time and leave just as easy. Overall the experience was great and I highly recommend.

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 👌.
Weekly house rentals

Windsor Castle 4-Bed + Garden
A real gem. Perfect location, clean and comfortable not to mention absolutely beautiful. Tim was always quick to respond and lovely to communicate with.

NEW Tornado Chase | Luxury 5 Bedroom Home
We had 4 adults, a 1 yr old and a 2 yr old at this location and it was great for the week we stayed with our family. There was plenty of space, it was clean with a nice open first floor, and the hosts were responsive whenever we had questions. Instructions were clear and helpful. Overall we had a lovely time and recommend this rental. Thank you!

Stylish Terraced House with Parking
Another pleasant stay at Elliot’s, lovely and comfortable place always spotless. Elliot is a great host, very reactive and flexible.

4 Bed - 3.5 Bath - Spacious Modern/Luxury Home
The house was just what we needed, 2 families staying with 3 kids. We spent most of our time out and about in Windsor and Legoland, but when we did get back, it was warm, clean and had a good size back garden to run around in. Parking was off street and enough for 2 cars as well which was helpful.

2 bedroom house in central Windsor
Great location. Nice space. Joanna was helpful!

Riverside Retreat
we were very happy with the stay at this location. the hosts left a very generous welcome basket - which wr took full advantage of. Once we figured out how to get to the riverfront the value of the location became clear. It is also super nice having a restaurant so close - picking up food there worked out well. we would definitely come back to this location! thank you.

Luxury Victorian Villa
We had a lovely stay in Windsor. Our hosts were extremely responsive and made us feel like we could just relax and enjoy our stay. The house also smelled amazing with these beautiful diffusers!

Detached 3 bed, driveway 4 cars
Lovely stay at Emma’s place. The house is clean and modern and lovely to have some bits for younger children to enjoy. Great location for our event and nice to be able to put children to bed and relax with family in comfortable surroundings
Private house rentals

Golfers’ retreat
Svetlana’s home is absolutely wonderful! She is incredibly kind and welcoming. The house has everything you need for a perfect stay — comfortable, well-equipped, and full of thoughtful details. The bed is super comfortable, which made my rest even better. What truly surprised me, and has never happened to me before in all my Airbnb stays, was finding some goodies waiting for me in the fridge. Such a lovely gesture! I highly recommend staying here.

Dee and Steve's ❤ A special place for your family!
Absolutely perfect! An easy walk to anything Windsor!. The place is everything described with a much better touch of home. Checking was super easy and Dee was available in an instant. THIS is what an AirBnB should be.

Central Windsor, Large Garden, Games Room & Office
Beautiful place, ideal for groups and families, well located to experience all the treasures of the Windsor area. I appreciated the key-lock arrangement, so that the key can be accessed and doesn't get lost. Beyond that, Mark supplied several instructional videos about how to operate some of the home's features. Beautiful, well laid out, top quality. I would have loved to welcome guests and family with me for the full value.

5* Charming 1-Bed Hideout,Comfort Meets Style Luxe
Absolute gem of a find. Super close to Windsor and legoland. Nikitas place is really nicely furnished, has everything you need for a few days away. The bed was the comfiest bed ever. Really great communication from Nikita and helped us a lot.

Home in Marlow
the house was fantastic and spotless, it is so close to Marlow town centre 5 min walk. Patricia is a great host, very friendly.

Gorgeous English Country Barn
Our stay at the Oak Barn at Hedsor was wonderful. The lodging itself is beautiful with large bedrooms and a huge sitting and dining area upstairs beneath the large oak beams. The location worked well as it allowed us to explore the Thames Valley and make two day trips into London. The estate property is beautiful, so do walk and note the different trees and plantings. We highly recommend this property and the people who live and work there.

Modern Home- 3beds/3 baths- Legoland/Ascot/Windsor
Tilehurst cottage is the perfect location to access attractions such as Windsor and Legoland. The house itself is wonderful- all the amenities you need, spotlessly clean and a lovely garden. My daughter is still talking about the pirate ship bedroom- she loved it! Also great space for spending time as a family, cooking and eating together and enjoying the garden. We also really appreciated the flexibility and responsiveness of Frederic and team re check in and answering questions during our stay Just brilliant, would highly recommend

Cottage in Hurst
A fantastic stay at Freya’s place, we were 4 adults, and felt very comfortable with plenty of space. The weather meant we got to use the garden, which is a lovely peaceful spot. Freya gave local recommendations, such as electric car charging and local taxi firms. Freya also helped out by going above and beyond when we requested some items, she brought them to the door. A perfect, seamless stay.
Quick stats about house rentals in Windsor and Maidenhead
Total rentals
1.1K properties
Total number of reviews
24K reviews
Family-friendly rentals
620 properties are a good fit for families
Pet-friendly rentals
260 properties allow pets
Rentals with a pool
20 properties have a pool
Rentals with dedicated workspaces
400 properties have a dedicated workspace
Destinations to explore
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- British Museum
- Green Park
- Buckingham Palace
- Covent Garden
- Big Ben
- Trafalgar Square
- Barbican Centre
- Harrods
- Tower Bridge
- London Bridge
- St. Paul's Cathedral
- Brockwell Park
- The O2
- Camden Market
- Emirates Stadium
- Wembley Stadium
- The Shard
- Hampstead Heath
- ExCeL London
- London Stadium
- River Lee Navigation
- Alexandra Palace
- Queen Elizabeth Olympic Park, London
- Oxford University