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
Cottage in Baughurst
4.95 out of 5 average rating, 308 reviewsLuxury rural thatched cottage with cedar hot tub.
Cottage in The Ayots
4.97 out of 5 average rating, 115 reviewsThe White Cottage Romantic Riverside Retreat
Cottage in Codicote
4.85 out of 5 average rating, 130 reviewsPrivate Hot Tub Getaway
Cottage in Berkshire
4.86 out of 5 average rating, 21 reviewsVintage style Lodge In Windsor! Hot Tub! Sleeps 20
Cottage in Wraysbury
4.82 out of 5 average rating, 153 reviewsOld Wharf Cottage - Riverside Living with Pool
Cottage in Ludgershall
1 Bed in Bicester Village (CLEAR)
Cottage in Surrey
4.9 out of 5 average rating, 105 reviewsDelightful Cottage 15 Acre Estate + Pool + Hottub
Cottage in Bracknell
4.82 out of 5 average rating, 33 reviews5* Luxury Stylish House -LONG STAY discount
Pet-friendly cottage rentals
Cottage in Ibworth
4.94 out of 5 average rating, 143 reviewsSelf contained, rural cottage, 2 double bedrooms
Cottage in Amersham, Bucks
4.98 out of 5 average rating, 121 reviewsDelightful, rural, modern cottage, large garden.
Cottage in Boxmoor
4.86 out of 5 average rating, 208 reviewsCute Cottage, Flint stone cottage, Hemel Hempstead
Cottage in Hookwood
4.84 out of 5 average rating, 420 reviewsDetached, 2 bed,easy access, single storey Cottage
Cottage in Oxfordshire
4.78 out of 5 average rating, 141 reviewsThe Granary country cottage with private garden
Cottage in Tilford
4.85 out of 5 average rating, 137 reviewsSquires Hill Cottage
Cottage in Fingest
4.82 out of 5 average rating, 178 reviewsHistoric Fairytale Cottage with 21stCentury Luxury
Cottage in Village
4.95 out of 5 average rating, 167 reviewsWimbledon Village Entire Cottage
Private cottage rentals
Cottage in Berkshire
4.93 out of 5 average rating, 229 reviewsBeautiful period cottage, Henley
Cottage in Colnbrook
4.9 out of 5 average rating, 111 reviews3 BR Victorian Cottage close to Windsor and Slough
Cottage in Englefield Green
4.9 out of 5 average rating, 162 reviewsLuxury 5* House Near Windsor Castle, Ascot, London
Cottage in Kingston upon Thames
4.97 out of 5 average rating, 153 reviewsStudio Cottage with garden
Cottage in Surrey
4.87 out of 5 average rating, 156 reviewsRiverside 2 bedroom home with private garden
Cottage in Ashford Hill
4.91 out of 5 average rating, 242 reviewsThatched Grade ll property in Ashford Hill
Cottage in Shalford
4.94 out of 5 average rating, 164 reviewsConverted dairy in Surrey Hills
Cottage in Crowmarsh Gifford
4.95 out of 5 average rating, 305 reviewsGardeners’ Cottage (Georgian stable conversion)
Quick stats about cottage rentals in Windsor and Maidenhead
Total rentals
70 properties
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
60 properties are a good fit for families
Total number of reviews
5.9K reviews
Nightly prices starting at
$50 before taxes and fees
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