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

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 stars2 weeks ago
Beautiful location, confortable and light room, peaceful neighbourhood away from town centre.
Guest favorite
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 stars2 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 stars32 months ago
Great location and property. Perfect stay
Top guest favorite
Cottage in Baughurst
4.96 out of 5 average rating, 370 reviews

Luxury rural thatched cottage with cedar hot tub.

SohrabRating, 5 stars1 week 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.
Top guest favorite
Cottage in Sarratt
5 out of 5 average rating, 236 reviews

Crestyl Cottage riverside barn for 2 with hot tub

KatieRating, 5 stars1 month ago
Beautiful area and nice little cottage, no complaints to be had.
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.

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 stars3 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 favorite
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!
Superhost
Cottage in Windsor and Maidenhead
4.76 out of 5 average rating, 140 reviews

Enchanting, Stylish Country Garden Cottage

RickRating, 5 stars1 month ago
We had a fantastic stay at Carina's property. Carina was very proactive in making sure we had all info needed to arrive stress free and have a good stay. Surrounding areas are as peaceful as it is beautiful.
Guest favorite
Cottage in Village
4.94 out of 5 average rating, 203 reviews

Wimbledon Village Sleeps 3 Cute Cottage

TimRating, 5 stars3 days ago
Super little (small, but perfectly formed) cottage in a cracking location. Really cute, very clean and the location can't be beaten. Loved the pretty terrace our front - private & peaceful, yet steps from the centre of the Wimbledon Village action.
Guest favorite
Cottage in Boxmoor
4.87 out of 5 average rating, 269 reviews

Cute Cottage, Flint stone cottage, Hemel Hempstead

StephenRating, 5 stars1 month ago
It was clean and we were happy for the big (about 50 foot/15m) garden to allow young kids to run around and play outside. The cottage has lots of space saving features, but would be tight for 6 people to stay long term with lots of time at the cottage.
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!
Superhost
Cottage in Chartridge
4.85 out of 5 average rating, 92 reviews

The Stables

AdamRating, 5 stars2 weeks ago
Fantastic place to stay, very cosy and comfortable. Comfy beds, modern bathroom, well decked out kitchen, Smart TV with all the apps, loads of storage in the bedrooms, ideal for our family of 4 staying for a week. Great location, on a quiet stretch of road, tucked away and private, but within easy driving distance of amenities. Great base for things to do in the area... Chesham itself is the last stop on the Metropolitan line which is ideal, only 8 mins drive from the cottage and cheap to park for the day. Its also a great spot to get to Harry Potter Warner Studios and Windsor which is why we chose it. Ellen was a fab host, lots of info sent through beforehand and responded quickly. We didn't need to bother her or her family whilst there, but we knew the offer was there if we needed it.

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 ⭐️
Top guest favorite
Cottage in Kingston upon Thames
5 out of 5 average rating, 51 reviews

Charming Coach House next to Richmond Park

RaganRating, 5 stars1 week ago
My husband and I stayed for a few nights over a weekend. The coach house is absolutely lovely. It is very comfortable, private, quiet, peaceful and was a nice respite from having spent time in busy London. You have everything you need to relax, sleep well and cook in. The place is nicely designed, tastefully decorated and clean. Petra greeted us upon arrival, showed us around and left us lovely provisions (decadent cakes!) to get us started on a nice weekend. We went for long walks/runs in Richmond Park (a 5 min walk away), and enjoyed hanging out in the house on a rainy Saturday. A large Sainsbury's is a 15-min walk away, and the Noribiton station is a 20 min walk. The coach house is located in a peaceful neighborhood with little traffic. We walked or took public transport. All in all, a fantastic, quiet getaway. We would definitely stay again.
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 Aldbury
4.91 out of 5 average rating, 107 reviews

Badgers Retreat, Aldbury, Tring

RichardRating, 5 stars1 month ago
5* stay with Debbie as always. We have been back several times and will continue to do so when working in the area
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 Mortimer Common
5 out of 5 average rating, 23 reviews

Cottage on edge of the village

IanRating, 5 stars4 days ago
Wow! My wife-to-be and her wedding party stayed at the lovely, characterful Stable Cottage for a couple of nights before and after our wedding. The cottage was superb, clean, well presented, decorated with tasteful colours and accessories, as well as some lovely old furnishings, which our party had little time to appreciate. The modern kitchen was well stocked, our hosts went above and beyond to provide a welcome and gifts (as they knew the purpose of or stay). Communications and attention to detail were faultless. It was very comfortable and relaxing, and the ladies couldn't have wished for more from the accommodation. There was even a lovely garden to enjoy, which unfortunately got rained on when we wanted it for photos! The only minor downside (for us) was the remoteness, and the slight difficulty with navigation to it, the latter resolved by the hosts with great guidance. We inadvertently gave them a cleaning challenge on checkout, which they handled with very good grace.

Quick stats about cottage rentals in Windsor and Maidenhead

  • Total rentals

    80 properties

  • Nightly prices starting at

    ﺩ.ﺇ184 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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