Cottage holiday rentals in Windsor and Maidenhead

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Popular amenities for cottage rentals in Windsor and Maidenhead

Pet-friendly cottage rentals

Guest favourite
Cottage
4.93 out of 5 average rating, 120 reviews

Farthings - genuine Austen charm cottage & garden

Carrie CRating, 5 stars4 days ago
Farthing Cottage was an absolute dream for a lover of all things English, Cadbury and cottage garden style. I arrived very late due to a train delay. Louise was very communicative and concerned on my behalf. She had lights on when I arrived. First thing on the spot - Malteser bunnies under a cake dome with chocolate easter egg cake! How did she know about me and maltesers/Cadbury! A welcome card also greeted me. The cottage has 17th century beams, lending a warm and cosy atmosphere. The fireplace had to be original and was gorgeous. Plenty of books, brochures and an instruction sheet. Living room was so cosy, I could have stayed there forever. Lovely furnishings. The master bedroom was sublime. Beautiful duvet and the bedframe appeared right out of Laura Ashley. Great bed and wonderful sleep. Louise couldn't have been more kind. Lovely neighbors. I couldn't get over that I could look out the window and see Jane Austen's house! My eyes welled up when it was time to go.
Guest favourite
Cottage
4.87 out of 5 average rating, 125 reviews

Fancy cottage by RiverThames , Kew Gardens

RuthRating, 5 stars3 weeks ago
We had a really good stay at Suzanne’s house. We were a party of 3 adults, 1 year old and a Labrador. Plenty of room with a lovely open plan space downstairs with very comfy seating in front of a great TV. The house was as described and in a lovely location just next to the river and across the road from Kew Green. The house is Suzanne’s home which was a bit strange as it does feel a bit intrusive, but it is clearly advertised as such and didn’t cause us any problems. Also lovely that it is dog friendly with loads of great dog walks near by. Thank you.
Superhost
Cottage
4.87 out of 5 average rating, 47 reviews

The Cottage, dog friendly,swimming pool in summer

OliverRating, 5 stars33 months ago
Miranda's cottage is very well situated and set up for doing as we did - enjoying the local area, taking advantage of hot summer days by the pool, and walking in the woods with kids. Highly recommended for families of 4 or even more if you're prepared to really use the space. My kids were very happy sleeping in the twin beds, and we were able to use every inch of the place.
Superhost
Cottage
4.77 out of 5 average rating, 134 reviews

Enchanting, Stylish Country Garden Cottage

NoneRating, 5 stars2 days ago
Carina was a good host and always available without being intrusive. The property is well priced and cosy with all the amenities required for an extended stay with lots to do on the doorstep in the beautiful area as well easily accessible links to the motorways to travel further afield. We visited the place and used it as a base as a family of 5 and spent a lot of the time out of the property as we were visiting family in the area. The amenities were great and we were able to wash the kids clothes that were getting dirty from all the outdoor activities available on the doorstep, we did a fair bit of walking in the surrounding country trails and went to legoland which is close by, the local pub was within walking distance and served fantastic food at a great price. I have nothing negative to say about the accommodation and host and would welcome another visit here, if I was to add a constructive appraisal would perhaps look to update the soft furnishings for a enhanced experience.
Guest favourite
Cottage
4.97 out of 5 average rating, 29 reviews

Country Cottage in Surrey Hills AONB

DelphineRating, 5 stars2 weeks ago
It was such a lovely stay at Lucy and Nick! Everything was perfect and all the family so lovely and welcoming. The cottage, the surroundings, the animals, the region, .. I will come back soon for sure!
Guest favourite
Cottage
4.94 out of 5 average rating, 198 reviews

Wimbledon Village Sleeps 3 Cute Cottage

PatrickRating, 5 stars3 weeks ago
Jennifer was great to work with and her cosy cottage is in an incredible location just few steps away from beautiful Wimbledon Village. Access to public transport was very easy. While it was somewhat tight quarters with three adults and a child, the space is very functional more than met our needs. We would not hesitate staying again in the future.
Top guest favourite
Cottage
4.97 out of 5 average rating, 115 reviews

Modern Cottage with Rural Views

TerryRating, 5 stars3 weeks ago
The house was lovely, freshly and tastefully decorated, with all you need for a week long stay. Elliot had left a few food items and the kinds of things you need to make cooking easy. The garden was secure for our dogs, and the nearby woods gave us somewhere to walk them easily. Henley was just a few minutes drive away, and Reading about 20 mins, so a great location for our needs. Plenty of easy parking right at the front door too. We travel to this area regulalry and will look to stay here again quite happily.
Guest favourite
Cottage
4.94 out of 5 average rating, 172 reviews

Self contained, rural cottage, 2 double bedrooms

DeeRating, 5 stars1 week ago
What a great setting for an escape to the country! I already miss waking up with the chickens and pigs to greet me every day. I also saw more wild animals and birds in my walks around here in a week, than I have in years in London. Auriol is a great host, relaxed, knowledgeable and friendly, and the property is exactly as described and shown here. Tips for other travelers: If you’re a light sleeper bring an eye mask and earplugs as it does get sunny in the main bedroom. Looking forward to returning here!

Private cottage rentals

Guest favourite
Cottage
4.91 out of 5 average rating, 433 reviews

Idyllic country cottage, close to central Oxford

DonaldRating, 5 stars2 weeks ago
This was an absolutely charming home. The hosts are kind and delightful. It's a perfect semi-rustic setting if you are looking for a comfortable country feel without being too far away from town. All the amenities you would want/need including good WiFi, washer/dryer. They even had some basic food items there awaiting for when we arrived! We hope to be back!
Top guest favourite
Cottage
4.99 out of 5 average rating, 99 reviews

The Coach House

LonnekeRating, 5 stars2 weeks ago
We had a lovely stay here. The house is pristine and very comfortable. Great welcome package on arrival. Great communication with Alison who went out of her way to make us feel welcome. Would love to come again. Thanks for having us!
Guest favourite
Cottage
4.97 out of 5 average rating, 114 reviews

Beautiful self catering 2 bed Cottage

StuartRating, 5 stars2 months ago
The place was great and acted as a great base to explore a lot of the local area and Legoland! The place was clean and exactly as described with no issues All communication was quick and all instructions clear. Great host. Would definitely recommend!
Top guest favourite
Cottage
4.98 out of 5 average rating, 91 reviews

Cosy luxury 3 bed cottage in The Surrey Hills

JeffRating, 5 stars5 days ago
Great experience, the place is better than the photos, and Amanda was so responsive and helpful. Highly recommend!
Guest favourite
Cottage
4.92 out of 5 average rating, 12 reviews

Hidden Cottage | Beautiful Esher, Surrey

LanceRating, 5 stars3 months ago
My family and I were in Esher visiting friends for the holidays and we couldn't have been happier with this cottage. It was beautifully decorated for the holidays and was a warm and inviting retreat from the British cold. It's very private, spacious (for our family of 4) and has all of the amenities that one would need for their stay. The communication process through the entire booking process and stay was excellent. If you are in the area and looking for a great rental, this is the place. We would not hesitate to stay here again!
Guest favourite
Cottage
4.98 out of 5 average rating, 60 reviews

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

CourtneyRating, 5 stars3 days ago
My family and I absolutely loved the location of Hollie and Daniel’s place. So central, everything walkable. Hollie was super responsive to any questions we had. The home is beautiful, bright, and very comfortable. We stayed with our 18 month old who very much enjoyed the spacious front porch area. We would definitely come back again!
Superhost
Cottage
4.86 out of 5 average rating, 83 reviews

Cosy Country Cottage

EdRating, 5 stars3 months ago
My daughter and her fiancée had a lovely couple of days in this gorgeous property. It was a perfect location for her to be able to show him where she grew up. They were very cosy (once they worked out how to get the heaters working). Highly recommended for a couples getaway.
Top guest favourite
Cottage
5 out of 5 average rating, 84 reviews

The Garden Cottage: Cosy weekend getaway.

JaneRating, 5 stars5 months ago
We were hiking the way of St James ( English Camino) and wanted a comfortable base to relax after a long days walking. This home exceeded our expectations. It was in a beautifully peaceful location, stand alone from their house, parking outside, walking distance to the pub. It had all the facilities we needed to cook, relax and sleep peacefully. Camilla and Tom were so welcoming, very responsive but also respectful of our privacy. It really is a special place, by far the best on our Camino, we highly recommend it.

Quick stats about cottage rentals in Windsor and Maidenhead

  • Total rentals

    80 properties

  • Nightly prices starting at

    £38 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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