Vacation rentals in Windsor and Maidenhead
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Top-rated vacation rentals in Windsor and Maidenhead
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
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Popular amenities for Windsor and Maidenhead vacation rentals
Other great vacation rentals in Windsor and Maidenhead
Guest favourite
Guest suite in Datchet
4.96 out of 5 average rating, 205 reviewsSelf Contained Annex, Datchet
Oct. 15 – 22
$131 CAD per night
Guest favourite
Guest suite in Warfield
4.92 out of 5 average rating, 180 reviewsThe Hayloft Suite, St Michaels Grange
Jun. 24 – Jul. 1
$178 CAD per night
Guest favourite
Guesthouse in Datchet
4.94 out of 5 average rating, 384 reviewsLuxury ♥️ 1 bed apartment Windsor Legoland Heathrow
Oct. 24 – 31
$188 CAD per night
Guest favourite
Cabin in Old Windsor
4.95 out of 5 average rating, 117 reviewsGorgeous Self-Contained Wooden Cabin - Old Windsor
Oct. 8 – 15
$143 CAD per night
Guest favourite
Guesthouse in Binfield
4.98 out of 5 average rating, 111 reviewsThe Brickmaker’s Loft
Mar. 16 – 23
$198 CAD per night
Guest favourite
Guesthouse in Bracknell Forest
4.99 out of 5 average rating, 158 reviewsSelf-contained Garden Lodge
Jun. 24 – Jul. 1
$113 CAD per night
Guest favourite
Apartment in Cookham
4.94 out of 5 average rating, 513 reviewsOld Butchers Wine Cellar 15th Century Apartment
Feb. 14 – 21
$239 CAD per night
Guest favourite
Condo in Marlow
4.98 out of 5 average rating, 194 reviewsCentral Marlow Apartment nr High St with Parking
Dec. 10 – 17
$195 CAD per night
Quick stats about vacation rentals in Windsor and Maidenhead
Total rentals
2.5K properties
Rentals with dedicated workspaces
990 properties have a dedicated workspace
Rentals with a pool
40 properties have a pool
Pet-friendly rentals
470 properties allow pets
Family-friendly rentals
1.2K properties are a good fit for families
Total number of reviews
62K reviews
Destinations to explore
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- Townhouse rentals Windsor and Maidenhead
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