
Cottage vacation rentals in Windsor and Maidenhead
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Top-rated cottage rentals in Windsor and Maidenhead
Guests agree: these cottages are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Windsor and Maidenhead cottage rentals
Cottage rentals with a hot tub

Newly Refurbished Tidy Room in a Cosy Cottage
Another lovely stay at Svetlana 's, clean and friendly highly recommend.

The Wabi-Sabi Sanctuary - Japanese Home & Hot Tub
Lovely peaceful place to stay. Authentic Japanese theme makes a refreshing and interesting cultural change. Care and love has gone into creating the Wabi Sabi Sanctuary.

Little 2 bedroom snug in Windsor with Hot Tub
Lovely, quiet and private place. Great host - highly recommend!

Rural Lodge stay In Windsor! Hot Tub! Sleeps 20
The place was absolutely beautiful and cozy feels like we’re just at home chilling. Every part of the room is spacious. Spotless clean. Backyard was big where we set up the party. Host was kind and responsive. We enjoyed our time spent in his place. Will definitely come back

5* Luxury Stylish House -LONG STAY discount
Great location and property. Perfect stay
Pet-friendly cottage rentals

Farthings - genuine Austen charm cottage & garden
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.

Fancy cottage by RiverThames , Kew Gardens
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.

The Cottage, dog friendly,swimming pool in summer
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.

Enchanting, Stylish Country Garden Cottage
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.

Country Cottage in Surrey Hills AONB
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!

Wimbledon Village Sleeps 3 Cute Cottage
Lovely house & surrounds. Really enjoyed our stay, thank you.

Modern Cottage with Rural Views
This was a fantastic place to stay. Great host, great location. Would definitely return

House with a View
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

Idyllic country cottage, close to central Oxford
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.

Beautiful Two Bedroom Cottage
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!

Charming Reigate/Redhill Cottage
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

Romantic cosy cottage close to Oxford & Le Manoir
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.)

Period cottage, cosy sittingroom individual host
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!

The Coach House
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.

Cosy luxury 3 bed cottage in The Surrey Hills
Great experience, the place is better than the photos, and Amanda was so responsive and helpful. Highly recommend!

Hidden Cottage | Esher | w/Parking
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
$69 CAD 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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- British Museum
- Green Park
- Kensington Gardens
- Big Ben
- Covent Garden
- Buckingham Palace
- Trafalgar Square
- Barbican Centre
- Harrods
- Tower Bridge
- St. Paul's Cathedral
- London Bridge
- Brockwell Park
- Camden Market
- Emirates Stadium
- Wembley Stadium
- The O2
- Hampstead Heath
- ExCeL London
- London Stadium
- Alexandra Palace
- Oxford University
- Blenheim Palace
- Silverstone Circuit