House holiday rentals in Windsor and Maidenhead

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Popular amenities for Windsor and Maidenhead house rentals

House rentals with a pool

Top Guest favourite
Home in Stadhampton
4.97 out of 5 average rating, 36 reviews

The Mill House

AlisonRating, 5 stars2 weeks ago
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.
Guest favourite
Home in Hammersmith
5 out of 5 average rating, 8 reviews

Spacious & stylish family home

NonnieRating, 5 stars2 months ago
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.
Superhost
Home in Ashmore Green

Berkshire country house with pool

PriyaRating, 5 stars17 months ago
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
Superhost
Home in Newdigate
5 out of 5 average rating, 4 reviews

Bright spacious home with natural swimming pond

NancyRating, 5 stars3 months ago
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.
Superhost
Home in Hammersmith
5 out of 5 average rating, 4 reviews

Pool & Piano | Hidden Oasis in Kensington Olympia

TanyaRating, 5 stars1 month ago
very nice and cooperative host. lovely place.
Superhost
Home in Oxfordshire
4.87 out of 5 average rating, 226 reviews

Barn conversion, Henley-on-Thames

AndrewRating, 5 stars3 days ago
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.
Superhost
Home in Greater London
5 out of 5 average rating, 4 reviews

The Place: 2-Bedroom Getaway

FarinaRating, 5 stars1 month ago
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.
Superhost
Home in Tadley
4.78 out of 5 average rating, 23 reviews

Stunning hideaway house

AidanRating, 5 stars23 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 👌.

Weekly house rentals

Superhost
Home in Berkshire
5 out of 5 average rating, 3 reviews

Windsor Castle 4-Bed + Garden

DeannaRating, 5 stars1 week ago
A real gem. Perfect location, clean and comfortable not to mention absolutely beautiful. Tim was always quick to respond and lovely to communicate with.
Top Guest favourite
Home in Berkshire
5 out of 5 average rating, 12 reviews

NEW Tornado Chase | Luxury 5 Bedroom Home

EmilyRating, 5 stars1 week ago
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!
Guest favourite
Home in Buckinghamshire
4.9 out of 5 average rating, 21 reviews

Stylish Terraced House with Parking

RichardRating, 5 stars1 month ago
Another pleasant stay at Elliot’s, lovely and comfortable place always spotless. Elliot is a great host, very reactive and flexible.
Superhost
Home in Eton Wick
4.81 out of 5 average rating, 42 reviews

4 Bed - 3.5 Bath - Spacious Modern/Luxury Home

DanielRating, 5 stars3 weeks ago
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.
Superhost
Home in Berkshire
4.89 out of 5 average rating, 45 reviews

2 bedroom house in central Windsor

KameronRating, 5 stars2 weeks ago
Great location. Nice space. Joanna was helpful!
Guest favourite
Home in Surrey
4.95 out of 5 average rating, 43 reviews

Riverside Retreat

ValerieRating, 5 stars1 week ago
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.
Superhost
Home in Berkshire
4.69 out of 5 average rating, 32 reviews

Luxury Victorian Villa

BrynRating, 5 starstoday
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!
Guest favourite
Home in Warfield
5 out of 5 average rating, 9 reviews

Detached 3 bed, driveway 4 cars

EmmaRating, 5 stars5 months ago
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

Top Guest favourite
Home in Sunningdale
5 out of 5 average rating, 13 reviews

Golfers’ retreat

YamilaRating, 5 stars1 month ago
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.
Superhost
Home in Windsor and Maidenhead
4.86 out of 5 average rating, 77 reviews

Dee and Steve's ❤ A special place for your family!

LoganRating, 5 stars1 week ago
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.
Top Guest favourite
Home in Windsor
5 out of 5 average rating, 20 reviews

Central Windsor, Large Garden, Games Room & Office

KathrynRating, 5 stars3 weeks ago
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.
Top Guest favourite
Home in Datchet
4.96 out of 5 average rating, 27 reviews

5* Charming 1-Bed Hideout,Comfort Meets Style Luxe

CharlotteRating, 5 stars2 weeks ago
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.
Top Guest favourite
Home in Buckinghamshire
5 out of 5 average rating, 62 reviews

Home in Marlow

PeterRating, 5 stars1 month ago
the house was fantastic and spotless, it is so close to Marlow town centre 5 min walk. Patricia is a great host, very friendly.
Guest favourite
Home in Hedsor
4.92 out of 5 average rating, 87 reviews

Gorgeous English Country Barn

PaulRating, 5 stars2 months ago
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.
Guest favourite
Home in Binfield
5 out of 5 average rating, 14 reviews

Modern Home- 3beds/3 baths- Legoland/Ascot/Windsor

EmmaRating, 5 stars1 month ago
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
Guest favourite
Home in Berkshire
4.91 out of 5 average rating, 46 reviews

Cottage in Hurst

VanessaRating, 5 stars1 day ago
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

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