Cottage vacation rentals in Windsor and Maidenhead

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Popular amenities for Windsor and Maidenhead cottage rentals

Cottage rentals with a hot tub

Top guest favorite
Cottage in Baughurst
4.96 out of 5 average rating, 371 reviews

Luxury rural thatched cottage with cedar hot tub.

SofiaRating, 5 stars1 day ago
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!
Guest favorite
Private room in Windsor and Maidenhead
4.88 out of 5 average rating, 56 reviews

Newly Refurbished Tidy Room in a Cosy Cottage

MarinaRating, 5 stars3 weeks ago
Beautiful location, confortable and light room, peaceful neighbourhood away from town centre.
Cottage in Shabbington

3 Bed in Shabbington (88963)

RikkiRating, 5 stars13 months ago
Great place to stay very secluded and private not a bad little boozer at the end of the lane either.
Top guest favorite
Cottage in Surrey
4.92 out of 5 average rating, 137 reviews

Delightful Cottage 15 Acre Estate + Pool + Hottub

IvanaRating, 5 stars1 month ago
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.
Cottage in Berkshire
4.67 out of 5 average rating, 27 reviews

Rural 2 bedroom lodge in Windsor with Hot Tub

AmyRating, 5 stars3 weeks ago
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.
Cottage in Berkshire
4.63 out of 5 average rating, 59 reviews

Rural Lodge stay In Windsor! Hot Tub! Sleeps 20

Ms Mofeyisope AishatRating, 5 stars1 month ago
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!
Cottage in Bracknell
4.82 out of 5 average rating, 33 reviews

5* Luxury Stylish House -LONG STAY discount

PaRating, 5 stars33 months ago
Great location and property. Perfect stay
Private room in Greater London

Cozy and Quiet Room to Rest

Pet-friendly cottage rentals

Guest favorite
Cottage in Englefield Green
5 out of 5 average rating, 29 reviews

Charming Stylish Cottage at Windsor Great Park

ChristyRating, 5 stars3 months ago
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.
Superhost
Cottage in Chiswick Riverside
4.87 out of 5 average rating, 126 reviews

Fancy cottage by RiverThames , Kew Gardens

JuliaRating, 5 stars1 month ago
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.
Superhost
Cottage in Windsor and Maidenhead
4.76 out of 5 average rating, 143 reviews

Enchanting, Stylish Country Garden Cottage

MartinRating, 5 stars1 week ago
Catrina’s place was amazing! Beautiful surroundings and very easy to get to local amenities (pub) Definitely stay again soon ❤️
Guest favorite
Cottage in Village
4.93 out of 5 average rating, 205 reviews

Wimbledon Village Sleeps 3 Cute Cottage

SusanRating, 5 stars6 days ago
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.
Top guest favorite
Cottage in Heath
4.98 out of 5 average rating, 123 reviews

Modern Cottage with Rural Views

RohitRating, 5 stars1 week ago
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!
Guest favorite
Cottage in Boxmoor
4.87 out of 5 average rating, 271 reviews

Cute Cottage, Flint stone cottage, Hemel Hempstead

KarenRating, 5 stars1 day ago
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.
Top guest favorite
Cottage in Amersham
4.99 out of 5 average rating, 139 reviews

Delightful, rural, modern cottage, large garden.

RebeccaRating, 5 stars3 weeks ago
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!
Guest favorite
Cottage in Ibworth
4.94 out of 5 average rating, 175 reviews

Self contained, rural cottage, 2 double bedrooms

HannahRating, 5 stars1 month ago
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

Top guest favorite
Cottage in Rotherwick
5 out of 5 average rating, 47 reviews

Private property in rural village

LukeRating, 5 stars1 month ago
Nicola was really friendly and helpful throughout, even left some bits for breakfast in the morning which you don’t see often. Thankyou for having us! 5 ⭐️
Guest favorite
Cottage in Ashford Hill
4.94 out of 5 average rating, 325 reviews

Thatched Grade ll property in Ashford Hill

MohamedRating, 5 stars2 weeks ago
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.
Top guest favorite
Cottage in Chilton
4.99 out of 5 average rating, 279 reviews

Cutter's Barn

MeganRating, 5 stars3 weeks ago
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
Guest favorite
Cottage in Berkshire
4.87 out of 5 average rating, 23 reviews

Walk to Windsor Castle-Grade II listed cottage

AndrewRating, 5 stars1 month ago
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.
Superhost
Cottage in Lyne
4.8 out of 5 average rating, 20 reviews

House with a View

WendyRating, 5 stars1 month ago
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!
Guest favorite
Cottage in Hurst
5 out of 5 average rating, 41 reviews

Fantastic self contained barn conversion in Hurst

KayRating, 5 stars4 months ago
Very clean and comfortable , with everything needed for a home from home while working nearby.
Guest favorite
Cottage in Eton
4.98 out of 5 average rating, 63 reviews

Design-Led-2xSuper-King Bed-2xEnsuites W Parking

StephanieRating, 5 stars1 month ago
Great place with fantastic location! The hosts were very helpful
Top guest favorite
Cottage in Sunninghill
4.96 out of 5 average rating, 28 reviews

Stunning 3 Bedroom, 2 bath Cottage in Ascot

LisaRating, 5 stars1 month ago
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

    R904 ZAR 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

Destinations to explore