Cottage holiday rentals in Windsor and Maidenhead

Find and book unique cottages on Airbnb

0 of 0 items showing
1 of 3 pages

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 stars1 week 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 stars1 month 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 stars34 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 stars1 week 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 stars4 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

PhilRating, 5 starstoday
Lovely house & surrounds. Really enjoyed our stay, thank you.
Top guest favourite
Cottage
4.97 out of 5 average rating, 116 reviews

Modern Cottage with Rural Views

AdamRating, 5 stars3 weeks ago
This was a fantastic place to stay. Great host, great location. Would definitely return
Superhost
Cottage
4.93 out of 5 average rating, 14 reviews

House with a View

louayRating, 5 stars3 weeks ago
Great holiday. Everything was beyond expectation. We did feel as real friends visiting the place. Highly appreciate. Strongly recommend for families looking for quality time. We injoyed Everything. Thanks for Julie's.

Private cottage rentals

Guest favourite
Cottage
4.91 out of 5 average rating, 435 reviews

Idyllic country cottage, close to central Oxford

NatashaRating, 5 stars2 weeks ago
We had a wonderful stay at Alison's cottage. It was perfect for our little multi-generational holiday. The location is great, 5 minutes walk to a great pub and the riverside. It feels very peaceful and rural, but also close to the city.
Top guest favourite
Cottage
4.96 out of 5 average rating, 27 reviews

Beautiful Two Bedroom Cottage

NicolaRating, 5 stars4 months ago
Mary-Ann was so helpful prior to the stay giving recommendations about places to eat. As we were there during a storm, we lost electricity and Mary-Ann went over and above delivering extra blankets, food and hot thermos. She also checked on us in the morning and delivered hot breakfast. Simply amazing, especially when there was nothing she could do about the national electricity outage. We can't wait to come back!
Superhost
Cottage
4.83 out of 5 average rating, 12 reviews

Charming Reigate/Redhill Cottage

DominicRating, 5 stars2 months ago
It’s honestly the first place we’ve stayed at I Reigate that felt homely and comfortable. The mattress was comfortable. The entire place feels warm. Well done David
Guest favourite
Cottage
4.95 out of 5 average rating, 66 reviews

Romantic cosy cottage close to Oxford & Le Manoir

KrisRating, 5 stars1 month ago
Idyllic cottage for weekend in Oxfordshire, with outstanding pub within walking distance, and very foodie area near Le Manoir. Very comfortable and welcoming, great kitchen for cooking, gorgeous garden for spring afternoons. Loved the little office space too. We did not want to leave! (Though when we did, it was only 6 miles to the center of Oxford.)
Guest favourite
Cottage
4.92 out of 5 average rating, 299 reviews

Period cottage, cosy sittingroom individual host

CRating, 5 stars4 days ago
We had a brief but lovely stay in the cottage. It was spacious, there were breakfast goodies for us and the bed was really comfortable. There was pretty countryside around and a meal at the Crown pub just down the road was a winner! Very easy communications, would recommend. Thanks Gilly & James!
Top guest favourite
Cottage
4.99 out of 5 average rating, 102 reviews

The Coach House

NicholasRating, 5 stars1 week ago
We were delighted with our stay at the Coach House. As well as being spotlessly clean it was furnished and decorated in a pleasing “ Country Chic” way, which was entirely appropriate. We loved the privacy and leafiness of the surroundings and woke to the sound of the dawn chorus and nothing else! Alison could not have been more helpful, but only came to us when needed. Highly recommended.
Top guest favourite
Cottage
4.98 out of 5 average rating, 91 reviews

Cosy luxury 3 bed cottage in The Surrey Hills

JeffRating, 5 stars2 weeks 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 | Esher | w/Parking

LanceRating, 5 stars4 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!

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

Destinations to explore