
Holiday houses in Windsor and Maidenhead
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Top-rated holiday rentals in Windsor and Maidenhead
Guests agree: these stays are highly rated for location, cleanliness and more.
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Top Guest favourite

Private room in Windsor and Maidenhead
5 out of 5 average rating, 31 reviewsEn-suite bedroom with free parking in Windsor
JoolsRating, 5 stars4 weeks ago
I really enjoyed my stay with Eloise and her family. The room was beautiful and such a comfortable bed and good shower. Eloise was very kind and helpful and even dropped me off into Windsor early one morning. I really enjoyed staying with Eloise and hope to go back and stay again soon.
Top Guest favourite

Private room in Windsor
4.94 out of 5 average rating, 127 reviewsSingle room/private bathroom/modern house +parking
BritaRating, 5 stars1 day ago
Paulina was super friendly and accommodating, and the house is gorgeous with a great garden. I only stayed for one night but would definitely come again. It’s a little trek to get in to Windsor, but depends on what you want to do.
Superhost

Private room in Maidenhead
4.82 out of 5 average rating, 561 reviewsDouble bedroom in Riverside home
DavidRating, 5 stars1 week ago
Catherine's place was perfect for me . It is a friendly and informal home , and the bedroom was comfortable , quiet and clean . The home is in a great position close to the river and a perfect starting point for long walks out to places like Windsor and Marlow . And with a large bathroom and shower at the end of the day , I had a perfectly relaxing and enjoyable stay . The home is in a leafy residential area , but the shops and restaurants of Maidenhead are easily accessible.
Top Guest favourite

Private room in Berkshire
4.98 out of 5 average rating, 105 reviewsDoll House - Sunny home
NinaRating, 5 stars1 week ago
Adrienne was really lovely. Her place is beautiful, quiet, and very clean. I’d definitely stay there again!
Guest favourite

Private room in Cookham
4.89 out of 5 average rating, 438 reviewsWarm, spacious loft room in Cookham
JanaRating, 5 stars3 weeks ago
ich war schon das 2.Mal bei Caroline und es war wieder sehr schön. Bis nach London ist man allerdings eine Weile unterwegs, aber die Zugverbindungen sind gut. Von dort bin ich super nach Oxford gefahren, auch sehr zu empfehlen. Die Ruhe ist einfach schön, auch wenn man ab und zu den Zug hört. Typisch britisch Gegend. Einkaufsmöglichkeiten gut. Bahnhof schnell zu erreichen.
Guest favourite

Private room in Maidenhead
4.96 out of 5 average rating, 336 reviewsGround floor room with own shower and kitchenette
LuluRating, 5 stars2 weeks ago
Sue was very nice and met me before check in to let me drop my bags off. The space is like a wee private apartment in her home, with a small kitchen and shower room. The bedroom overlooks a lovely garden. The accommodation is very near the bit of the Thames that’s like a canal, full of geese and barges and so pretty in the spring. It’s a bit of a walk to the town centre and no markets nearby. I wanted to cook but there was no oil or seasonings so you’d have to buy all those things.
Top Guest favourite

Private room in Maidenhead
4.95 out of 5 average rating, 82 reviewsLarge, airy double bedroom.
BethRating, 5 stars1 week ago
It was a great few nights. Chris was very welcoming. Her flat is lovely, clean and very comfortable. It was just what I needed working away from home. Hopefully stay again soon.
Top Guest favourite

Private room in Holyport
5 out of 5 average rating, 68 reviewsHome Room (sizeable double room & private shower)
MariellaRating, 5 stars2 weeks ago
I visited the Airbnb of Joanne because I had a masterclass in Waltham nearby. The room and facilities as well as Joanne, her husband and the dogs where wonderful! I felt at home immediately. In addition, from Maidenhead station it is easy to reach. Uber is still driving in the area so you in a few minutes you will have transportation. I had a great stay and will definitely come again in case I have another masterclass or work at the same location!
Quick stats about holiday rentals in Windsor and Maidenhead
Total rentals
2.5K properties
Total number of reviews
72K reviews
Family-friendly rentals
1.2K properties are a good fit for families
Pet-friendly rentals
500 properties allow pets
Rentals with a pool
50 properties have a pool
Rentals with dedicated workspaces
990 properties have a dedicated workspace
Destinations to explore
- River Thames Holiday rentals
- Royal Borough of Kensington and Chelsea Holiday rentals
- London Borough of Camden Holiday rentals
- City of Westminster Holiday rentals
- London Holiday rentals
- Central London Holiday rentals
- Regent's Canal Holiday rentals
- London Borough of Islington Holiday rentals
- South London Holiday rentals
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- Oxford Holiday rentals
- Inner London Holiday rentals
- Rentals with a washing machine and dryer Windsor and Maidenhead
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- House rentals Windsor and Maidenhead
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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