
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 Windsor and Maidenhead cottage rentals
Cottage rentals with a hot tub

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

The Wabi-Sabi Sanctuary - Japanese Themed Home
A very comfortable stay for a night away, hot tub was lovely, Yumi was a great host with near immediate responses, kitchen was well equipped with a nice reception area attached so we never felt apart from each other. Would recommend

The White Cottage Romantic Riverside Retreat
The White Cottage is a truly magical experience, and combined with Sally’s as the perfect host, we came away from our short break with memories that will last a lifetime. The location is breathtakingly peaceful. A garden within a garden set in landscape where time has good still. The stream that runs through garden is a playground for wildlife and you’ll be sharing your breakfast with ducks and moorhens. If you want a break oozing peace and quiet, a chance to unwind, and forget the day to day life the white cottage has it spades. Sally is a delightful host. Nothing is too much trouble. You arrive as a guest and leave as a friend. We loved it

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.

Hillview
Fantastic stay here with my girlfriend . We both found the place incredibly relaxing and was so easy to feel at home . The surroundings our beautiful and really peaceful . Highly recommend for a couples retreat

Chic country cottage, hot tub & wood burning stove
Had a good stay and used the location as a base to explore the North Wessex Downs. The house itself was as described and the kids enjoyed the hot tub. Large garden for kids to run around in.

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

Luxury rural thatched cottage with cedar hot tub.
My friends and I enjoyed a peaceful couple of nights in Jean and Kieth's beautiful cottage. Keith was friendly and helpful with clear instructions. the cottage is gorgeous and the garden is lovely! I would definitely stay there again.
Pet-friendly cottage rentals

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.

Farthings - genuine Austen charm cottage & garden
This beautiful old cottage was an absolute treat to stay in for the weekend. Louise has thought of every detail, so we felt at home and had all we needed for our stay. Chawton is a gorgeous village and we did several of the activities that are local to it (Jane Austen's House, Chawton House, the Watercress Line steam train). The Greyfriars pub is a few doors down and we had a super evening meal in there (it was a busy Saturday night, so it was lucky that we'd booked in advance). Louise was very communicative and helpful and she very kindly allowed us to stay a little later on our day of departure. We loved our stay, thank you!

Coldharbour Farmhouse
We had a great few nights here on the run up to our son’s wedding at a nearby venue. The house was fantastic as a multi generational base and everyone loved the quirkyness of it. Supper on the patio was heaven. Positives were the location, peaceful surroundings and the beauty of the house. Only slight negative was the size of the beds that we felt could have been bigger ( the rooms are great sizes)

Cosy 2 bedroom cottage in West Hanney village
Had a great stay here and everything was perfect. We managed to try the only local pub and the food and beer was excellent and value for money. The Indian restaurant was better than and from my local area in Stockport. The location is great for Oxford and we did a day trip to the Diddly Squat Farm. Tracey is a great host and we would definitely stay here again next time we are in the area.

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.

Elegant Countryside Cottage near Oxford
A most pleasing cottage in a superb setting of an idealistic English village. Hosts excellent A cosy living area and spacious bedroom with adjoining dressing room leading to a superb bathroom with high quality curved glass shower cubical. In short the nicest private accommodation out of dozens we have enjoyed.

Cute Cottage, Flint stone cottage, Hemel Hempstead
we had a wonderful stay at the cute cottage. everything was really comfortable and relaxing. we are looking forward to returning. we recommend this cute cottage

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

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.

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 ❤️

Converted dairy in Surrey Hills
Dagley Cottage is well situated within a lovely area. Its spacious arrangement has everything needed for a comfortable stay and is a great base to return to. Joanna is a great host offering good communication both before and during the stay. A special place.

Beautifully renovated cottage - Prince's Forge
We enjoyed our stay very much. Kitchen and living are very comfortable and the beds offered a refreshing sleep. It may take a while for the shower to be warm, but the bathroom was clean and complete. Great place to stay. Great atmosphere and a beautiful area to walk. Vanessa was very hospitable and helpful when needed.

St Albans Grove - 1 Bed Cottage in Kensington
Location is terrific. Henry is a very responsive host. Check-in was easy. The staircase is a little challenging as is stated in the description. The hot water in the shower great and plenty of water pressure. All in all, a lovely place to stay and the location unbeatable.

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

Charming 2 bedroom cottage with own garden
Lovely and charming cottage. The home was very clean and it had everything we needed. Extra blanket and duvets were a plus! Had a drink at the pub next door. And while we didn’t visit any other pubs, there was another within walking distance. Easy and quick communication with the host. Thank you for our stay!
Quick stats about cottage rentals in Windsor and Maidenhead
Total rentals
80 properties
Nightly prices starting at
$77 AUD 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