Cottage holiday rentals in Windsor and Maidenhead

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Popular amenities for Windsor and Maidenhead cottage rentals

Cottage rentals with a hot tub

Guest favourite
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.
Guest favourite
Cottage in Beacon Hill
5 out of 5 average rating, 6 reviews

The Wabi-Sabi Sanctuary - Japanese Themed Home

MatthewRating, 5 stars2 weeks ago
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
Guest favourite
Cottage in The Ayots
4.97 out of 5 average rating, 142 reviews

The White Cottage Romantic Riverside Retreat

JohnRating, 5 stars2 weeks ago
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
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 Rudgwick
5 out of 5 average rating, 4 reviews

Hillview

OliRating, 5 stars1 week ago
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
Guest favourite
Cottage in Sutton Scotney
4.88 out of 5 average rating, 475 reviews

Chic country cottage, hot tub & wood burning stove

SamuelRating, 5 stars2 months ago
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.
Cottage in Bracknell
4.82 out of 5 average rating, 33 reviews

5* Luxury Stylish House -LONG STAY discount

PaRating, 5 stars32 months ago
Great location and property. Perfect stay
Top Guest favourite
Cottage in Baughurst
4.96 out of 5 average rating, 370 reviews

Luxury rural thatched cottage with cedar hot tub.

SohrabRating, 5 stars2 weeks ago
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

Superhost
Cottage in Chiswick Riverside
4.87 out of 5 average rating, 126 reviews

Fancy cottage by RiverThames , Kew Gardens

JuliaRating, 5 stars4 weeks 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.
Guest favourite
Cottage in Chawton
4.93 out of 5 average rating, 122 reviews

Farthings - genuine Austen charm cottage & garden

BethanRating, 5 stars1 month ago
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!
Guest favourite
Cottage in Turners Hill
4.9 out of 5 average rating, 104 reviews

Coldharbour Farmhouse

HRating, 5 stars1 day ago
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)
Guest favourite
Cottage in West Hanney
4.95 out of 5 average rating, 144 reviews

Cosy 2 bedroom cottage in West Hanney village

GillianRating, 5 stars3 weeks ago
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.
Guest favourite
Cottage in Village
4.94 out of 5 average rating, 204 reviews

Wimbledon Village Sleeps 3 Cute Cottage

SusanRating, 5 stars5 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 favourite
Cottage in Brill
4.88 out of 5 average rating, 127 reviews

Elegant Countryside Cottage near Oxford

JamesRating, 5 stars2 weeks ago
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.
Guest favourite
Cottage in Boxmoor
4.87 out of 5 average rating, 270 reviews

Cute Cottage, Flint stone cottage, Hemel Hempstead

GregoryRating, 5 stars1 week ago
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
Guest favourite
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

Guest favourite
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 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 favourite
Cottage in Shalford
4.94 out of 5 average rating, 170 reviews

Converted dairy in Surrey Hills

PeterRating, 5 stars9 months ago
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.
Top Guest favourite
Cottage in Peasemore
4.98 out of 5 average rating, 211 reviews

Beautifully renovated cottage - Prince's Forge

VictorRating, 5 stars1 week ago
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.
Guest favourite
Cottage in Greater London
4.91 out of 5 average rating, 126 reviews

St Albans Grove - 1 Bed Cottage in Kensington

MariaRating, 5 stars3 weeks ago
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.
Guest favourite
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 favourite
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 favourite
Cottage in Stoke Mandeville
5 out of 5 average rating, 169 reviews

Charming 2 bedroom cottage with own garden

AngelaRating, 5 stars6 days ago
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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