Windsor and Maidenhead Vacation Rentals

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

From US $315 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 US $489 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 US $499 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 US $1,316 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 US $374 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 US $156 per night
10.0 (1 Review)
2 Bedrooms 4 Guests
10.0 (5 Reviews)
2 Bedrooms 6 Guests
From US $194 per night
10.0 (5 Reviews)
1 Bedroom 4 Guests
10.0 (5 Reviews)
2 Bedrooms 6 Guests
From US $642 per night
10.0 (4 Reviews)
3 Bedrooms 6 Guests
10.0 (4 Reviews)
3 Bedrooms 6 Guests
From US $373 per night
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9.9 (22 Reviews)
1 Bedroom 2 Guests
From US $392 per night
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10.0 (2 Reviews)
1 Bedroom 4 Guests
From US $374 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 US $238 per night
10.0 (2 Reviews)
1 Bedroom 2 Guests
10.0 (1 Review)
3 Bedrooms 6 Guests
From US $235 per night
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9.8 (89 Reviews)
1 Bedroom 2 Guests
From US $358 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 US $319 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 US $125 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 US $239 per night
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9.8 (5 Reviews)
1 Bedroom 2 Guests

About Windsor and Maidenhead Vacation Rentals

With more than 1020 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 645.61 ft² on average, with prices averaging US $353 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 1020 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.