You can go into the Windows.old files and get anything that you want to keep. I rely on this feature to keep all my documents, pictures, contacts, bookmarks and such. Then after I have copied everything I want to save into their respective files I remove the whole Windows.old file.
The way you remove it is to call up the Windows Disk Cleanup program. Have it scan your system drive. Then after it does that click on the "Clean Up System Files" button. Have it scan again and it will bring up the Windows.old file. Check mark it and have it delete it. If you just try to delete the file Windows won't let you.
Operating System Windows 7 Ultimate x64
Computer Type Laptop
CPU Type and Speed Intel Core i5 430m dualcore
Motherboard Chipset Inspiron 1764 Intel HM55 Chipset
System Memory Type 4 GB DDR3-1066 SDRAM
Video Card Type and Speed Intel Graphics Media Accelerator HD HDMI
Computer Monitor 17.3" HD Laptop monitor
Hard Drive 3B29 WDC WD5000BEVT-75ZAT0 ATA 465 GB IDE
Optical Drives Optiarc DVD+-RW AD-7585H ATA
Network Adapter Realtek PCIe FE Family Network Controller + Dell 1520 Wireless-N Mini-Card
Anti-virus Software ESET Smart Security v4
Computer Skill Level Self-Taught Expert