Find Vacation Rentals in Windsor and Maidenhead

We have 1,491 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
$270 per night
House ∙ 5 guests ∙ 3 bedrooms
5.0
Outstanding (2 ratings)
Windsor, Windsor and Maidenhead, United Kingdom
Details
Vrbo
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Details
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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Cabin Wraysbury
$233 per night
Cabin ∙ 2 guests ∙ 1 bedroom
5.0
Outstanding (31 ratings)
Wraysbury, Windsor and Maidenhead, United Kingdom
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Vrbo
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Details
Apartment Windsor
$164 per night
Apartment ∙ 2 guests ∙ 2 bedrooms
5.0
Outstanding (1 rating)
Windsor, Windsor and Maidenhead, United Kingdom
Details
Vrbo
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Apartment Maidenhead
$105 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Maidenhead, Windsor and Maidenhead, United Kingdom
Details
Vrbo
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House Windsor
$277 per night
House ∙ 6 guests ∙ 2 bedrooms
4.9
Outstanding (32 ratings)
Windsor, Windsor and Maidenhead, United Kingdom
Details
Vrbo
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House Windsor
$469 per night
House ∙ 8 guests ∙ 4 bedrooms
5.0
Outstanding (15 ratings)
Windsor, Windsor and Maidenhead, United Kingdom
Details
Vrbo
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House Wraysbury
$272 per night
House ∙ 7 guests ∙ 3 bedrooms
4.9
Outstanding (20 ratings)
Wraysbury, Windsor and Maidenhead, United Kingdom
Details
Vrbo
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Apartment Windsor
$150 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
4.8
Outstanding (30 ratings)
Windsor, Windsor and Maidenhead, United Kingdom
Details
Vrbo
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Recommended Rentals With Pools

Cottage  Sunningdale
-20%
$1,678
$1,347 per night
Cottage ∙ 14 guests ∙ 7 bedrooms
Sunningdale, Windsor and Maidenhead, United Kingdom
Pool
Details
HomeToGo
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Apartment  Windsor
$154 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
4.7
Excellent (24 ratings)
Windsor, Windsor and Maidenhead, United Kingdom
Pool
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Vrbo
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Details
Cottage  Wraysbury
$1,023 per night
Cottage ∙ 10 guests ∙ 5 bedrooms
5.0
Outstanding (6 ratings)
Wraysbury, Windsor and Maidenhead, United Kingdom
Pool
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Vrbo
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Pet-Friendly Homes and Apartments

Apartment  Windsor
$182 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
3.3
(7 ratings)
Windsor, Windsor and Maidenhead, United Kingdom
Pet-friendly
Details
Vrbo
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House  White Waltham
$346 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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House  Wraysbury
$190 per night
House ∙ 4 guests ∙ 2 bedrooms
4.3
Very good (139 ratings)
Wraysbury, Windsor and Maidenhead, United Kingdom
Pet-friendly
Details
Vrbo
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Best vacation rentals with a balcony

House  Windsor
$359 per night
House ∙ 4 guests ∙ 2 bedrooms
Windsor, Windsor and Maidenhead, United Kingdom
Balcony
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Vrbo
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Details
Apartment  White Waltham
$255 per night
Apartment ∙ 2 guests ∙ 1 bedroom
White Waltham, Windsor and Maidenhead, United Kingdom
Balcony
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Vrbo
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Boat  Wraysbury
$203 per night
Boat ∙ 3 guests ∙ 1 bedroom
5.0
Outstanding (4 ratings)
Wraysbury, Windsor and Maidenhead, United Kingdom
Balcony
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Vrbo
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Details
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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 $85.

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

There are 1,491 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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