Windsor and Maidenhead Vacation Rentals

Compare Vacation Rentals & Rent By Owner Homes in Windsor and Maidenhead, England, United Kingdom

From CA $437 per night
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10.0 (4 Reviews)
1 Bedroom 2 Guests
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10.0 (12 Reviews)
3 Bedrooms 7 Guests
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10.0 (3 Reviews)
1 Bedroom 2 Guests
From CA $679 per night
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10.0 (2 Reviews)
1 Bedroom 2 Guests
10.0 (22 Reviews)
1 Bedroom 2 Guests
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10.0 (7 Reviews)
2 Bedrooms 4 Guests
10.0 (17 Reviews)
1 Bedroom 2 Guests
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10.0 (4 Reviews)
1 Bedroom 2 Guests
10.0 (17 Reviews)
1 Bedroom 3 Guests
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10.0 (3 Reviews)
4 Bedrooms 10 Guests
10.0 (14 Reviews)
4 Bedrooms 8 Guests
10.0 (3 Reviews)
4 Bedrooms 8 Guests
10.0 (3 Reviews)
3 Bedrooms 5 Guests
From CA $694 per night
10.0 (11 Reviews)
4 Bedrooms 8 Guests
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10.0 (2 Reviews)
2 Bedrooms 4 Guests
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10.0 (2 Reviews)
1 Bedroom 2 Guests
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10.0 (2 Reviews)
2 Bedrooms 4 Guests
From CA $1,829 per night
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10.0 (1 Review)
5 Bedrooms 10 Guests
10.0 (7 Reviews)
4 Bedrooms 10 Guests
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10.0 (1 Review)
2 Bedrooms 4 Guests
10.0 (7 Reviews)
2 Bedrooms 6 Guests
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10.0 (1 Review)
2 Bedrooms 4 Guests
10.0 (6 Reviews)
5 Bedrooms 11 Guests
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10.0 (1 Review)
4 Bedrooms 8 Guests
10.0 (5 Reviews)
4 Bedrooms 9 Guests
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10.0 (1 Review)
3 Bedrooms 5 Guests
From CA $520 per night
10.0 (5 Reviews)
3 Bedrooms 6 Guests
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10.0 (1 Review)
1 Bedroom 2 Guests
10.0 (5 Reviews)
2 Bedrooms 4 Guests
From CA $217 per night
10.0 (1 Review)
2 Bedrooms 4 Guests
10.0 (5 Reviews)
2 Bedrooms 6 Guests
From CA $269 per night
10.0 (5 Reviews)
1 Bedroom 4 Guests
10.0 (5 Reviews)
2 Bedrooms 6 Guests
From CA $892 per night
10.0 (4 Reviews)
3 Bedrooms 6 Guests
10.0 (4 Reviews)
3 Bedrooms 6 Guests
From CA $518 per night
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9.9 (22 Reviews)
1 Bedroom 2 Guests
From CA $545 per night
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10.0 (2 Reviews)
1 Bedroom 4 Guests
From CA $520 per night
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10.0 (2 Reviews)
1 Bedroom 2 Guests
10.0 (1 Review)
2 Bedrooms 4 Guests
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9.8 (99 Reviews)
2 Bedrooms 4 Guests
From CA $331 per night
10.0 (2 Reviews)
1 Bedroom 2 Guests
10.0 (1 Review)
3 Bedrooms 6 Guests
From CA $327 per night
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9.8 (89 Reviews)
1 Bedroom 2 Guests
From CA $498 per night
10.0 (1 Review)
2 Bedrooms 4 Guests
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9.8 (20 Reviews)
1 Bedroom 2 Guests
10.0 (1 Review)
1 Bedroom 4 Guests
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9.8 (19 Reviews)
5 Bedrooms 10 Guests
From CA $443 per night
10.0 (1 Review)
2 Bedrooms 6 Guests
10.0 (1 Review)
4 Bedrooms 7 Guests
9.8 (11 Reviews)
3 Bedrooms 6 Guests
10.0 (1 Review)
2 Bedrooms 4 Guests
9.8 (7 Reviews)
2 Bedrooms 4 Guests
10.0 (1 Review)
2 Bedrooms 4 Guests
From CA $174 per night
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9.8 (6 Reviews)
11 Bedrooms 22 Guests
10.0 (1 Review)
2 Bedrooms 5 Guests
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9.8 (5 Reviews)
1 Bedroom 2 Guests
10.0 (1 Review)
2 Bedrooms 3 Guests
From CA $332 per night
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9.8 (5 Reviews)
1 Bedroom 2 Guests

About Windsor and Maidenhead Vacation Rentals

With more than 1022 Windsor and Maidenhead vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rent By Owner Homes (RBOs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an RBO property in Windsor and Maidenhead.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Windsor and Maidenhead, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (RBOs), and other popular Airbnb-style properties in Windsor and Maidenhead. Places to stay near Windsor and Maidenhead are 644.91 ft² on average, with prices averaging CA $489 a night.

RentByOwner makes it easy and safe to find and compare vacation rentals in Windsor and Maidenhead with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Frequently Asked Questions About Windsor and Maidenhead?

What are the top vacation rentals in Windsor and Maidenhead?

How many Rentbyowner vacation rentals are available in Windsor and Maidenhead?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 1022 in the Windsor and Maidenhead area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Windsor and Maidenhead.