Find Vacation Rentals in Windsor and Maidenhead

We have 1,065 properties to choose from
Windsor and Maidenhead
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Windsor and Maidenhead
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Popular Windsor and Maidenhead Vacation Rentals

Find the perfect Windsor and Maidenhead vacation rental

House Windsor and Maidenhead
$216 per night
House ∙ 5 guests ∙ 3 bedrooms
Windsor and Maidenhead, England, United Kingdom
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Vrbo
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Apartment Maidenhead
$83 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Maidenhead, Windsor and Maidenhead, United Kingdom
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Vrbo
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House Windsor
$56 per night
House ∙ 3 guests ∙ 1 bedroom
Windsor, Windsor and Maidenhead, United Kingdom
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Vrbo
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House Windsor
$265 per night
House ∙ 5 guests ∙ 3 bedrooms
5.0
Outstanding (2 ratings)
Windsor, Windsor and Maidenhead, United Kingdom
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Vrbo
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Apartment Windsor
$159 per night
Apartment ∙ 2 guests ∙ 1 bedroom
4.9
Outstanding (12 ratings)
Windsor, Windsor and Maidenhead, United Kingdom
Details
Vrbo
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House Wraysbury
$150 per night
House ∙ 7 guests ∙ 3 bedrooms
4.9
Outstanding (18 ratings)
Wraysbury, Windsor and Maidenhead, United Kingdom
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Vrbo
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Cottage Windsor
$175 per night
Cottage ∙ 7 guests ∙ 2 bedrooms
5.0
Outstanding (3 ratings)
Windsor, Windsor and Maidenhead, United Kingdom
Details
Vrbo
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House Windsor
$239 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding (2 ratings)
Windsor, Windsor and Maidenhead, United Kingdom
Details
Vrbo
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House Wraysbury
$192 per night
House ∙ 4 guests ∙ 2 bedrooms
4.3
Very good (144 ratings)
Wraysbury, Windsor and Maidenhead, United Kingdom
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Vrbo
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Recommended Rentals With Pools

Cottage  Sunningdale
$1,365 per night
Cottage ∙ 14 guests ∙ 7 bedrooms
Sunningdale, Windsor and Maidenhead, United Kingdom
Pool
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HomeToGo
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Apartment  Windsor
$147 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
4.7
Excellent (23 ratings)
Windsor, Windsor and Maidenhead, United Kingdom
Pool
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Vrbo
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Cottage  Wraysbury
$755 per night
Cottage ∙ 10 guests ∙ 5 bedrooms
5.0
Outstanding (5 ratings)
Wraysbury, Windsor and Maidenhead, United Kingdom
Pool
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Vrbo
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Pet-Friendly Homes and Apartments

Apartment  Windsor
$198 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
3.3
(7 ratings)
Windsor, Windsor and Maidenhead, United Kingdom
Pet-friendly
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Vrbo
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Apartment  Windsor
$134 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding (4 ratings)
Windsor, Windsor and Maidenhead, United Kingdom
Pet-friendly
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Vrbo
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House  White Waltham
$335 per night
House ∙ 10 guests ∙ 4 bedrooms
5.0
Outstanding (6 ratings)
White Waltham, Windsor and Maidenhead, United Kingdom
Pet-friendly
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Vrbo
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Best vacation rentals with a balcony

Apartment  Hurley
$208 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
Hurley, Windsor and Maidenhead, United Kingdom
Balcony
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HomeToGo
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Apartment  Maidenhead
$280 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Maidenhead, Windsor and Maidenhead, United Kingdom
Balcony
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Vrbo
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House  Windsor
$703 per night
House ∙ 12 guests ∙ 6 bedrooms
5.0
Outstanding (4 ratings)
Windsor, Windsor and Maidenhead, United Kingdom
Balcony
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Vrbo
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Frequently Asked Questions

Is renting a vacation home in Windsor and Maidenhead expensive?

The price per night in Windsor and Maidenhead starts at $50.

Can I see all vacation rentals that are available in Windsor and Maidenhead?

There are 1,065 vacation rental offers in Windsor and Maidenhead available to book.

Finding the perfect vacation home has never been easier. Tripping.com searches the world's top vacation rental sites to find the best properties in 190 countries worldwide. One search lets you filter, compare and sort over 10 million available vacation rentals from trusted partners including HomeAway, VRBO, TripAdvisor, Booking.com and more. When you use Tripping.com to plan your trip and book your vacation rental, you never have to wonder if you're getting the best deal.

Vacation Rentals in Maidenhead

Looking for a vacation rental in Maidenhead? Tripping.com has 168 vacation rental homes available in Maidenhead. You'll find 0 studios, 126 1-bedroom, 31 2-bedroom and 11 rentals with 3 or more bedrooms ranging from $28 a night. For extra convenience, many of these vacation homes can be booked directly online. The average price of a nightly rental in Maidenhead is $141 while the average price of a weekly rental is $25. For those looking for more than a short term rental such as corporate rentals, extended stays or long term rentals, the average monthly price of a Maidenhead home is $25. Wondering if you can bring your dog or cat along with you? There are 22 pet-friendly vacation rentals available in Maidenhead. In addition to accommodating pets, Maidenhead rentals offer a variety of amenities. In particular, 151 rentals have Internet and WiFi, 143 have TV and/or cable and 18 have a pool or hot tub. Search properties from 6 vacation rental sites in Maidenhead where the top providers in that area are Booking.com, Expedia, and TripAdvisor. There are 53 Booking.com rentals, 46 Expedia short term rentals and 29 TripAdvisor vacation rentals.

Homes & Vacation Rentals

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