
Cottage holiday rentals in Windsor and Maidenhead
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Top-rated cottage rentals in Windsor and Maidenhead
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Popular amenities for cottage rentals in Windsor and Maidenhead
Cottage rentals with a hot tub

Luxury rural thatched cottage with cedar hot tub.
We had a wonderful stay at this beautiful house, cozy yet spacious and with an amazing garden. It was the perfect spot to celebrate a birthday, enjoy the sunshine, relax in the hot tub, and gather around the firepit and BBQ. Keith and Jean were very welcoming and kindly showed us around, even though we arrived late. A fantastic place, we highly recommend it!

Newly Refurbished Tidy Room in a Cosy Cottage
Beautiful location, confortable and light room, peaceful neighbourhood away from town centre.

3 Bed in Shabbington (88963)
Great place to stay very secluded and private not a bad little boozer at the end of the lane either.

Delightful Cottage 15 Acre Estate + Pool + Hottub
Felt very welcome lovely cosy place for a family Tanya made us a delicious cookies which we really enjoyed it was very nice of her to take her time out and make us delicious treat,the pool and jacuzzi was the best part for my son enjoyed every bit of it Tanya is very lovely host wouldn’t think twice to come back thank you for a enjoyable weekend.

Rural 2 bedroom lodge in Windsor with Hot Tub
Our first time using Air bnb and our first time to Windsor and Central London. I am so glad we found this place. We definitely would come back here again. It was everything we were looking for. Everything was clean, all essentials were included. The bed was very comfortable. The host was quick to respond to messages. We loved the hot tub and the private garden. Only 4 minutes to Aldi, Close to Windsor town, close to Legoland which was amazing even in the rain, they sell Legoland ponchos so people can enjoy whatever the weather.

Rural Lodge stay In Windsor! Hot Tub! Sleeps 20
We had a lovely stay, the house was beautiful and exceeded our expectations. Istvan was also a very kind and accommodating host who was highly responsive at all times. Would definitely recommend booking for your get away or holiday!

5* Luxury Stylish House -LONG STAY discount
Great location and property. Perfect stay

Cozy and Quiet Room to Rest
Pet-friendly cottage rentals

Charming Stylish Cottage at Windsor Great Park
We thoroughly enjoyed our stay at Fox Hollow Cottage, such care and attention to detail has been put into the design of this space, it is a real gem of a property. Also being located adjacent to Great Windsor Park, it’s an idyllic location for everyone who loves a good walk, jog or bike. Ben was also a very attentive host. It’s possible the steep stairs up to the bedrooms could be an issue for some, however I would definitely stay again and recommend to others.

Fancy cottage by RiverThames , Kew Gardens
We enjoyed our stay at the Fancy Cottage in Kew. Suzanne's cottage was close to Kew Gardens and just steps to the Thames Path as advertised. We enjoyed having our coffee in the sunny breakfast area or eating in after a day of activities. Bedrooms were good sized and it was great having two bathrooms. Easy walk to nice restaurants in Kew. Easy access to Richmond and London by bus or tube. Overall, very peaceful place to stay and enjoy Kew with easy access to all London has to offer.

Enchanting, Stylish Country Garden Cottage
Catrina’s place was amazing! Beautiful surroundings and very easy to get to local amenities (pub) Definitely stay again soon ❤️

Wimbledon Village Sleeps 3 Cute Cottage
Jennifer’s place is an adorable little cottage. We loved our stay there; the house was perfect for us and right in the heart of Wimbledon Village. Fantastic delis; especially the large Italian one right round the corner and Paul’s Bakery also on the high street. I would definitely stay there again and 100% recommend this property.

Modern Cottage with Rural Views
This was our second stay at one of Elliot’s Airbnbs, and once again, it was a great experience. Elliot is a fantastic host, professional, helpful, and very understanding. The house has a warm, positive vibe and was spotless on arrival. He had kindly kept essentials like milk, bread, and more, which was a thoughtful touch, especially appreciated by our 10-year-old son. The nearby restaurant is lovely too. Overall, a really comfortable and pleasant stay. Highly recommended!

Cute Cottage, Flint stone cottage, Hemel Hempstead
Lovely little cottage. It was nice to have a garden especially as it was very hot. The fans provided were a nice touch. Good base for visiting Warner Brothers Studios.

Delightful, rural, modern cottage, large garden.
We had a wonderful stay here, the cottage was really clean with everything you could need including lovely toiletries/soap/hand creams, a well equipped kitchen and tennis rackets for the court outside. It was located in a really peaceful area, with easy access to paths straight from the cottage. Lots of choice of places to eat nearby . The outside space was great, our children loved having a go on the tennis court and we even saw a deer in the garden! Georgie was quick to respond to pur questions, helpful and offered flexibility around check in/out. we would definitely come back!

Self contained, rural cottage, 2 double bedrooms
We stayed at The Twig whilst visiting family in the area and it was absolutely perfect for our needs. The cottage was spacious, clean and the animals were an added bonus especially for our 3 year old daughter. We will definitely be back when next visiting the area, thank you!
Private cottage rentals

Private property in rural village
We had a wonderful time in Nicola’s place, the accommodation, the location and hospitality was second to none. Would fully recommend for an event in the “Village Hall”. Superb host Nicola thank you so much x

Thatched Grade ll property in Ashford Hill
We really loved our stay in this little cottage. A perfect get away for 2. Philippa was very friendly and accommodating and the little breakfast trays were a bonus! Easy to find with clear instructions and in a peaceful area. Overall, a lovely place to stay.

Cutter's Barn
I stayed at this air bnb for my wedding at a nearby venue. It was the best! I felt so relaxed, the host was very friendly and we had the best time! I would highly recommend staying here

Walk to Windsor Castle-Grade II listed cottage
Lovely house in a great location. Easy walk into Windsor and the castle, with option to go via the Long Walk. Lots of options for food & drink nearby. The pub around the corner has nice outside seating. Permit parking on the streets is a little inconvenient but the multi-storey car park is less than 5 minute walk and had plenty of space (large spaces by UK standards too). Dee was very responsive to the couple of questions we had.

House with a View
Nice English Cottage with a big back yard! Very convenient check in hour! On site parking is a plus! Though Lyne Lane near the Cottage is kind of dangerous to get in and out! The mirror on the pole opposite to the drive way does little to help! Anyhow, my family enjoyed our stay!

Fantastic self contained barn conversion in Hurst
Very clean and comfortable , with everything needed for a home from home while working nearby.

Design-Led-2xSuper-King Bed-2xEnsuites W Parking
Great place with fantastic location! The hosts were very helpful

Stunning 3 Bedroom, 2 bath Cottage in Ascot
We had a wonderful weekend. The house is fabulous,it had every amenity you could think of. The kitchen was fully equipped. large lounge/ dining room plenty of space and beautifully decorated. Close enough to walk into the village but very peaceful. I highly recommend staying here.
Quick stats about cottage rentals in Windsor and Maidenhead
Total rentals
80 properties
Nightly prices starting at
$64 SGD before taxes and fees
Total number of reviews
5.8K reviews
Family-friendly rentals
60 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
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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